Naratriptan hydrochloride supplier

Name
NARATRIPTAN HYDROCHLORIDE (125 MG)F0C3600.998MG/MG(AI)
EINECS
CAS No. 143388-64-1
Article Data8
CAS DataBase
Density
Solubility
Melting Point 234-236 °C
Formula C₁₇H₂₆ClN₃O₂S
Boiling Point 541.3 °C at760mmHg
Molecular Weight 371.931
Flash Point 281.2 °C
Transport Information
Appearance Beige solid
Safety 26
Risk Codes 36
Molecular Structure
Hazard Symbols Xi
Synonyms 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochloride (9CI);Amerge;GR85548A;N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamidehydrochloride;Naramig;UNII-10X8X4P12Z;
PSA 73.58000
LogP 4.28040

Synthetic route

: 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;

palladium oxide on charcoal: palladium oxide on charcoal

: 166306-28-1
N-methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulphonamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
In hydrogenchloride; methanesulfonic acid; water	88%
With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide
With hydrogenchloride In water; ethyl acetate; N,N-dimethyl-formamide

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Stage #1: N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; platinum(IV) oxide In methanol at 50 - 60℃; under 3677.86 Torr; Stage #2: With hydrogenchloride In ethanol; isopropyl alcohol for 1h; Product distribution / selectivity; Reflux;	85%
Multi-step reaction with 2 steps 1.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 1.2: 10 °C / pH 7.5 - 8.5 2.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

palladium oxide on charcoal: palladium oxide on charcoal

: 166306-29-2
(E)-N-Methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethene sulphonamide, hydrochloride

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
In methanol; water; ethyl acetate; N,N-dimethyl-formamide	71.2%

: C18H24N3O4S(1-)*Na(1+)

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water for 12h; pH=2; Product distribution / selectivity; Heating / reflux;

palladium oxide on charcoal: palladium oxide on charcoal

: 166306-28-1
N-methyl-2-[3-(1,2,3,6-tetrahydro-1-methyl-4-pyridinyl)-1H-indol-5-yl]ethenesulphonamide

: 7440-44-0
pyrographite

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate; N,N-dimethyl-formamide
With hydrogenchloride In ethyl acetate; N,N-dimethyl-formamide

...Expand

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 8 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 8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
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 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 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 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: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 9 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 9.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

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

: 143388-64-1
naratriptan hydrochloride

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 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 6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 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 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 5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 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
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
6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
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 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
5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
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: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

Yield

Multi-step reaction with 7 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
7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

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: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

: 1268265-95-7
N-[4-(2-{methylsulfamoyl}ethyl)-2-{2-(trimethylsilanyl)ethynyl}phenyl]acetamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium hydroxide; ethanol / 15 - 25 °C 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 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 5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 1.2: 0.5 h / 25 °C 2.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 2.2: 10 - 15 °C / pH 8 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 3.2: 10 °C / pH 7.5 - 8.5 4.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

Yield

Multi-step reaction with 5 steps
1.1: potassium hydroxide; ethanol / 15 - 25 °C
2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
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
5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

Multi-step reaction with 4 steps
1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere
1.2: 0.5 h / 25 °C
2.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
2.2: 10 - 15 °C / pH 8
3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
3.2: 10 °C / pH 7.5 - 8.5
4.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

: 1268265-97-9
2-(4-benzylamino-3-trimethylsilanylethynyl-phenyl)ethanesulfonic acid methylamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: potassium hydroxide; ethanol / 15 - 25 °C 2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 3.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 4.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 4.2: 25 - 30 °C 4.3: 10 - 15 °C 5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 5.2: 10 °C / pH 7.5 - 8.5 6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 5 steps 1: potassium hydroxide; ethanol / 15 - 25 °C 2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 3: potassium hydroxide / methanol / 8 h / 60 - 65 °C 4: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 5: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

Yield

Multi-step reaction with 6 steps
1.1: potassium hydroxide; ethanol / 15 - 25 °C
2.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
3.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
4.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C
4.2: 25 - 30 °C
4.3: 10 - 15 °C
5.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr
5.2: 10 °C / pH 7.5 - 8.5
6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

Multi-step reaction with 5 steps
1: potassium hydroxide; ethanol / 15 - 25 °C
2: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
3: potassium hydroxide / methanol / 8 h / 60 - 65 °C
4: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
5: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

: 1268265-99-1
N-[2-ethynyl-4-(2-(methylsulfamoyl)ethyl)phenyl]acetamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 1.2: 0.5 h / 25 °C 2.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 2.2: 10 - 15 °C / pH 8 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 3.2: 10 °C / pH 7.5 - 8.5 4.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

Yield

Multi-step reaction with 4 steps
1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
1.2: 0.5 h / 25 °C
2.1: trifluoroacetic acid / ethanol / 25 °C / Reflux
2.2: 10 - 15 °C / pH 8
3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 1448.05 - 2172.08 Torr
3.2: 10 °C / pH 7.5 - 8.5
4.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

: 1268266-01-8
2-(4-benzylamino-3-ethynylphenyl)ethanesulfonic acid methylamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 2.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 3.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 3.2: 25 - 30 °C 3.3: 10 - 15 °C 4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 4.2: 10 °C / pH 7.5 - 8.5 5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 4 steps 1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 2: potassium hydroxide / methanol / 8 h / 60 - 65 °C 3: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 4: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

Yield

Multi-step reaction with 5 steps
1.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
2.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C
3.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C
3.2: 25 - 30 °C
3.3: 10 - 15 °C
4.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr
4.2: 10 °C / pH 7.5 - 8.5
5.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

Multi-step reaction with 4 steps
1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C
2: potassium hydroxide / methanol / 8 h / 60 - 65 °C
3: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C
4: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1
View Scheme

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 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 4.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 3: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

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

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 1.2: 10 °C / pH 7.5 - 8.5 2.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

: 1200070-42-3
2-(4-amino-3-iodo-phenyl)ethanesulfonic acid methylamide

: 143388-64-1
naratriptan hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: dichloromethane / 1.5 h / 25 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium hydroxide; ethanol / 15 - 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 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 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 6 steps 1.1: dichloromethane / 1.5 h / 25 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 25 - 85 °C / Inert atmosphere 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 6.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 7 steps 1.1: methanol / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium hydroxide; ethanol / 15 - 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 6.1: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C 7.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme
Multi-step reaction with 8 steps 1.1: methanol / 25 - 30 °C 1.2: 4 h / 25 - 30 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium hydroxide; ethanol / 15 - 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 6.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 6.2: 25 - 30 °C 6.3: 10 - 15 °C 7.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 7.2: 10 °C / pH 7.5 - 8.5 8.1: hydrogenchloride / isopropyl alcohol; acetone / 5 - 10 °C / pH 1 View Scheme

: 143388-64-1
naratriptan hydrochloride

: 2-[4-formylamino-3-(1-methylpiperidine-4-carbonyl)phenyl]ethanesulphonic acid methylamide

Conditions

Conditions	Yield
With sodium periodate In methanol at 20℃; for 68.5h;	76%

: 1-((4-azido)phenylthio)pyrrolidine-2,5-dione

: 143388-64-1
naratriptan hydrochloride

: 2-(2-(4-azidophenyl)thio-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl)-N-methylethanesulfonamide

Conditions

Conditions	Yield
With 2-((-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)carbamoyl)-3,4,5,6-tetrachlorobenzoic acid; trifluoroacetic acid In methanol; dichloromethane; water at 20℃; for 24h;	49%

: 143388-64-1
naratriptan hydrochloride

: 1-methyl-5'-(2-(N-methylsulfamoyl)ethyl)-2'-oxo-1-azaspiro[bicyclo[2.2.1]heptane-7,3'-indolin]-1-ium iodide

Conditions

Conditions	Yield
With water; iodine; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 20h; chemoselective reaction;	24%

: 143388-64-1
naratriptan hydrochloride

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With sodium hydroxide In water

Naratriptan hydrochloride Chemical Properties

IUPAC Name: N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamidehydrochloride
Following is the structure of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1):

Empirical Formula: C₁₇H₂₆ClN₃O₂S
Molecular Weight: 371.9252
Flash Point: 281.2 °C
Melting point: 234-236 °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
Appearance of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1): Beige Solid
Product Categories of 1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1): Intermediates & Fine Chemicals; Pharmaceuticals
Canonical SMILES: CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C.Cl
InChI: InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
InChIKey: AWEZYKMQFAUBTD-UHFFFAOYSA-N

Naratriptan hydrochloride Uses

1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) (CAS NO.143388-64-1) is a triptan drug and is used for the treatment of migraine headaches.

Naratriptan hydrochloride Specification

1H-Indole-5-ethanesulfonamide,N-methyl-3-(1-methyl-4-piperidinyl)-, hydrochloride (1:1) , its cas register number 143388-64-1. It also can be called Naratriptan hydrochloride ; Amerge ; GR 85548A ; Monohydrochloride ; Naratriptan HCl ; Naratriptan hydrochloride ; UNII-10X8X4P12Z ; and N-Methyl-3-(1-methylpiperidin-4-yl)-1H-indole-5-ethanesulfonamide hydrochloride . Its classification code is Antimigraine.

Product Name

NARATRIPTAN HYDROCHLORIDE (125 MG)F0C3600.998MG/MG(AI)

Synthetic route

Naratriptan hydrochloride Chemical Properties

Naratriptan hydrochloride Uses

Naratriptan hydrochloride Specification

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