Naratriptan supplier | CasNO.121679-13-8

Name
Naratriptan
EINECS
CAS No. 121679-13-8
Article Data11
CAS DataBase
Density 1.227 g/cm³
Solubility
Melting Point 170-171°
Formula C₁₇H₂₅N₃O₂S
Boiling Point 541.3 °C at 760 mmHg
Molecular Weight 335.47
Flash Point 281.2 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide;Naratriptan(Amerge);
PSA 73.58000
LogP 3.47840

Synthetic route

: 894351-87-2
N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran for 0.166667h;	84%
Stage #1: N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; palladium 10% on activated carbon at 25℃; under 724.026 Torr; Stage #2: With ammonia In water at 10℃; pH=7.5 - 8.5;

: 639008-15-4
2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With sodium In tetrahydrofuran; ammonia at -78℃; for 0.75h;	80%

: 121679-20-7
N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 35℃; Product distribution / selectivity;	73.3%
With hydrogen; palladium 10% on activated carbon In ethanol; N,N-dimethyl-formamide at 25 - 35℃; under 2206.72 Torr; for 2h; Product distribution / selectivity;	72.7%
With 5% Pd(II)/C(eggshell); hydrogen; acetic acid In methanol; water at 25 - 35℃; under 6840.46 - 7600.51 Torr; Reactivity; Reagent/catalyst; Solvent; Time;	64%

: 1-benzyl-1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-piperidinium bromide

A: 121679-13-8
naratriptan

B: 220392-03-0
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
With lithium triamylborohydride In tetrahydrofuran for 26h; dequaternisation; Heating;	A n/a B 44%

: 1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-1-(1-phenyl-ethyl)piperidinium bromide

A: 121679-13-8
naratriptan

B: 220392-08-5
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at 60℃; for 22h; dequaternisation; Title compound not separated from byproducts;

: 894351-85-0
2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 2: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 3: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 2.2: 25 - 30 °C 2.3: 10 - 15 °C 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 3.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme

: 894351-84-9
2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 2: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 3: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 4: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

: 894351-86-1
2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 2: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme
With triethylsilane; ethanol; hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃;
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 1.2: 25 - 30 °C 1.3: 10 - 15 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme

: 63263-84-3
N-benzylindoline-5-carboxaldehyde

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C 2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.2: 73 percent / tetrahydrofuran / -78 - 0 °C 3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C
2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C
2.2: 73 percent / tetrahydrofuran / -78 - 0 °C
3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr
4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C
5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr
6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h
View Scheme

: 63263-88-7
1-benzyl-1H-indole-5-carbaldehyde

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 73 percent / tetrahydrofuran / -78 - 0 °C 2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

Yield

Multi-step reaction with 5 steps
1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C
1.2: 73 percent / tetrahydrofuran / -78 - 0 °C
2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr
3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C
4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr
5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h
View Scheme

: 1445-73-4
1-Methyl-4-piperidone

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: 52148-00-2
trans-2-(p-nitrophenyl)ethenesulfonyl chloride

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C
2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
6: 84 percent / KOH / methanol / 2 h / 20 °C
7: 83 percent / KOH / methanol / 8 h / Heating
8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 555-16-8
4-nitrobenzaldehdye

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 86 percent / t-BuOK / tetrahydrofuran / 4.5 h / -78 °C 2: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 3: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 4: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 5: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 6: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 7: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 8: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 9: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 10: 84 percent / KOH / methanol / 2 h / 20 °C 11: 83 percent / KOH / methanol / 8 h / Heating 12: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 13: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme
Multi-step reaction with 10 steps 1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C 2: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C 3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 7: 84 percent / KOH / methanol / 2 h / 20 °C 8: 83 percent / KOH / methanol / 8 h / Heating 9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 86 percent / t-BuOK / tetrahydrofuran / 4.5 h / -78 °C
2: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C
3: 0.7 g / NaI*2H2O / acetone / 6 h / Heating
4: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating
5: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C
6: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
7: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
8: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
9: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
10: 84 percent / KOH / methanol / 2 h / 20 °C
11: 83 percent / KOH / methanol / 8 h / Heating
12: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
13: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

Multi-step reaction with 10 steps
1: 100 percent / n-BuLi / tetrahydrofuran; hexane / 4.5 h / -78 °C
2: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C
3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
7: 84 percent / KOH / methanol / 2 h / 20 °C
8: 83 percent / KOH / methanol / 8 h / Heating
9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 2-(4-nitrophenyl)ethenesulfonic acid isopropyl ester

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 2: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 3: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 4: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 5: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 6: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 7: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 8: 84 percent / KOH / methanol / 2 h / 20 °C 9: 83 percent / KOH / methanol / 8 h / Heating 10: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 11: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 0.7 g / NaI*2H2O / acetone / 6 h / Heating
2: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating
3: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C
4: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
5: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
6: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
7: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
8: 84 percent / KOH / methanol / 2 h / 20 °C
9: 83 percent / KOH / methanol / 8 h / Heating
10: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
11: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 639008-17-6
2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid isopropyl ester

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 2: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 3: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 4: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 5: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 6: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 7: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 8: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 9: 84 percent / KOH / methanol / 2 h / 20 °C 10: 83 percent / KOH / methanol / 8 h / Heating 11: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 12: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C
2: 0.7 g / NaI*2H2O / acetone / 6 h / Heating
3: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating
4: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C
5: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
6: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
7: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
8: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
9: 84 percent / KOH / methanol / 2 h / 20 °C
10: 83 percent / KOH / methanol / 8 h / Heating
11: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
12: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 639008-01-8
2-(4-nitrophenyl)ethenesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 2: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 3: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 4: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 5: 84 percent / KOH / methanol / 2 h / 20 °C 6: 83 percent / KOH / methanol / 8 h / Heating 7: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 8: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
2: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
3: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
4: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
5: 84 percent / KOH / methanol / 2 h / 20 °C
6: 83 percent / KOH / methanol / 8 h / Heating
7: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
8: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 639008-03-0
2-(4-aminophenyl)ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 2: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 3: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 4: 84 percent / KOH / methanol / 2 h / 20 °C 5: 83 percent / KOH / methanol / 8 h / Heating 6: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 7: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
2: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
3: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
4: 84 percent / KOH / methanol / 2 h / 20 °C
5: 83 percent / KOH / methanol / 8 h / Heating
6: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
7: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 639008-13-2
N-benzyl-2-(1H-indole-5-yl)-N-methylethane-1-sulfonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 83 percent / KOH / methanol / 8 h / Heating 2: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 3: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: 639008-16-5
2-hydroxy-2-(4-nitrophenyl)ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 85 percent / triethylamine; methanesulfonyl chloride / CH2Cl2 / 24.17 h / 0 - 5 °C
2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
6: 84 percent / KOH / methanol / 2 h / 20 °C
7: 83 percent / KOH / methanol / 8 h / Heating
8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 639008-08-5
2-[4-(2,2-dimethoxyethylamino)phenyl]ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 2: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 3: 84 percent / KOH / methanol / 2 h / 20 °C 4: 83 percent / KOH / methanol / 8 h / Heating 5: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 6: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: 639008-12-1
2-[1-(2,2,2-trifluoroacetyl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / KOH / methanol / 2 h / 20 °C 2: 83 percent / KOH / methanol / 8 h / Heating 3: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 4: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: 639008-14-3
2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 2: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: 639008-10-9
N-{4-[2-(benzylmethylsulfamoyl)ethyl]phenyl}-N-(2,2-dimethoxyethyl)-2,2,2-trifluoroacetamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 2: 84 percent / KOH / methanol / 2 h / 20 °C 3: 83 percent / KOH / methanol / 8 h / Heating 4: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 5: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

: sodium 2-(4-nitrophenyl)ethenesulfonate

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 2: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 7: 84 percent / KOH / methanol / 2 h / 20 °C 8: 83 percent / KOH / methanol / 8 h / Heating 9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating
2: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C
3: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr
4: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C
5: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C
6: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C
7: 84 percent / KOH / methanol / 2 h / 20 °C
8: 83 percent / KOH / methanol / 8 h / Heating
9: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr
10: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C
View Scheme

: 4-hydrazino-N-methyl-benzenethanesulphonamide

: 10333-64-9
1-methyl-4 (formylmethyl)piperidine

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With hydrogenchloride; polyphosphate ester; sodium carbonate In chloroform; water

: 98623-16-6
2-(4-amino-phenyl)ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.2: 0.5 h / 25 °C 6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 6.2: 10 - 15 °C / pH 8 7.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 7.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 4.2: 0.5 h / 25 °C 5.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 5.2: 10 - 15 °C / pH 8 6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 6.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 7 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: methanol / 25 - 30 °C 2.2: 4 h / 25 - 30 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 7.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme
Multi-step reaction with 8 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: methanol / 25 - 30 °C 2.2: 4 h / 25 - 30 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 6.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 7.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 7.2: 25 - 30 °C 7.3: 10 - 15 °C 8.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 8.2: 10 °C / pH 7.5 - 8.5 View Scheme

: 98623-50-8
N-Methyl-1H-indole-5-ethanesulphonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 1.2: 10 - 15 °C / pH 8 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme

: 1268265-90-2
N-[2-iodo-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 3.2: 0.5 h / 25 °C 4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 4.2: 10 - 15 °C / pH 8 5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 5.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 4 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 2.2: 0.5 h / 25 °C 3.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 3.2: 10 - 15 °C / pH 8 4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 4.2: 10 °C / pH 7.5 - 8.5 View Scheme

Yield

Multi-step reaction with 5 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
3.2: 0.5 h / 25 °C
4.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
4.2: 10 - 15 °C / pH 8
5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
5.2: 10 °C / pH 7.5 - 8.5
View Scheme

Multi-step reaction with 4 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere
2.2: 0.5 h / 25 °C
3.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
3.2: 10 - 15 °C / pH 8
4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
4.2: 10 °C / pH 7.5 - 8.5
View Scheme

: 1268265-93-5
2-(4-benzylamino-3-iodophenyl)ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 5.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 5.2: 25 - 30 °C 5.3: 10 - 15 °C 6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 6.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 5 steps 1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 1.2: 25 °C 2.1: potassium hydroxide; ethanol / 15 - 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 5.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
5.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C
5.2: 25 - 30 °C
5.3: 10 - 15 °C
6.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr
6.2: 10 °C / pH 7.5 - 8.5
View Scheme

Multi-step reaction with 5 steps
1.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C
1.2: 25 °C
2.1: potassium hydroxide; ethanol / 15 - 25 °C
3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
4.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
5.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
View Scheme

: 585-71-7, 38661-81-3
(1-bromoethyl)benzne

: 121679-13-8
naratriptan

: 1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-1-(1-phenyl-ethyl)piperidinium bromide

Conditions

Conditions	Yield
In acetone at 50℃; for 260h; quaternisation;	100%

: 100-39-0
benzyl bromide

: 121679-13-8
naratriptan

: 1-benzyl-1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-piperidinium bromide

Conditions

Conditions	Yield
In acetone quaternisation;	99%

: 20710-47-8
[13C2H3] methyl iodide

: 121679-13-8
naratriptan

: C17(13)CH25(2)H3N3O2S(1+)*I(1-)

Conditions

Conditions	Yield
In acetone at 20℃; for 18h; quaternisation;	95%

: 121679-13-8
naratriptan

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 30℃; for 1h; pH=1.0 - 1.5; Product distribution / selectivity;	93.4%
With hydrogenchloride In methanol; water at 0 - 10℃;	84%
With hydrogenchloride In methanol; ethanol at 5 - 25℃; pH=1.0;	71.7%
With hydrogenchloride In isopropyl alcohol; acetone at 5 - 10℃; pH=1;

: 121679-13-8
naratriptan

: 220392-08-5
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / acetone / 260 h / 50 °C 2: lithium tri-sec-butylborohydride / tetrahydrofuran / 22 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / acetone / 260 h / 50 °C 2: lithium trisecbutylborohydride / tetrahydrofuran / 70 h / Heating View Scheme

: 121679-13-8
naratriptan

: 220392-03-0
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / acetone 2: 44 percent / lithium trisamylborohydride / tetrahydrofuran / 26 h / Heating View Scheme

Naratriptan Chemical Properties

IUPAC name: N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Molecular Formula: C₁₇H₂₅N₃O₂S
Molecular Weight: 335.464300 g/mol
Index of Refraction: 1.605
Surface Tension: 51.3 dyne/cm
Density: 1.227 g/cm³
Flash Point: 281.2 °C
Enthalpy of Vaporization: 81.91 kJ/mol
Boiling Point: 541.3 °C at 760 mmHg
Vapour Pressure: 8.81E-12 mmHg at 25 °C
Product Categories: Indoline & Oxindole
Following is the structure of Naratriptan (CAS NO.121679-13-8):

Naratriptan Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
women	TDLo	oral	3750ug/kg/22W (3.75mg/kg)	BEHAVIORAL: HEADACHE	Lancet. Vol. 353, Pg. 378, 1999.

Naratriptan Specification

Naratriptan , its cas register number is 121679-13-8. It also can be called N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide ; 1H-indole-5-ethanesulfonamide, N-Methyl-3-(1-methyl-4-piperidinyl)- naratriptan .
Naratriptan (trade names include Amerge and Naramig) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. Naratriptan is available in 2.5 mg tablets. It is a selective 5-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-( 1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide.

Product Name

Naratriptan

Synthetic route

Naratriptan Chemical Properties

Naratriptan Toxicity Data With Reference

Naratriptan Specification

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