rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 45℃; for 0.25h; pH=13 - 14; | 96% |
With sodium hydroxide In water; toluene at 45℃; for 0.25h; Product distribution / selectivity; | 92% |
With sodium hydroxide In water pH=11.98; Product distribution / selectivity; | n/a |
(R)-tert-butyl 2,3-dihydro-1H-inden-1-yl(prop-2-ynyl)carbamate
rasagiline
Conditions | Yield |
---|---|
Stage #1: (R)-tert-butyl 2,3-dihydro-1H-inden-1-yl(prop-2-ynyl)carbamate With hydrogenchloride; water In 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water Inert atmosphere; | 95% |
rasagiline mesylate
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In water at 3 - 5℃; for 1h; pH=7.5 - 11; Product distribution / selectivity; | 91.6% |
With sodium hydroxide In water at 3 - 5℃; pH=11; | 91.6% |
With sodium hydroxide In water; toluene pH=~ 14; | |
With sodium hydroxide In water; toluene pH=14; |
R-(+)-N-propargyl-1-aminoindane L-(+)-mandelate
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide | 90% |
(R)-N-(2-chloroallyl)-2,3-dihydro-1H-inden-1-amine
rasagiline
Conditions | Yield |
---|---|
With sodium t-butanolate In ISOPROPYLAMIDE at 0 - 5℃; for 2.16667h; Product distribution / selectivity; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 60℃; for 16h; | 79% |
With potassium carbonate In acetonitrile at 60℃; for 16h; |
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 30 - 50℃; Product distribution / selectivity; | 74.56% |
propargyl benzenesulfonate
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In toluene at 30℃; for 29h; | 65.8% |
With sodium hydroxide In toluene at 30℃; for 29h; | 65.8% |
Stage #1: (R)-2,3-dihydro-1H-inden-1-amine hydrochloride With tetrabutylammomium bromide; sodium hydroxide In water at 15 - 20℃; for 0.25h; Stage #2: propargyl benzenesulfonate In water at 15 - 20℃; for 2.75h; | |
Stage #1: (R)-2,3-dihydro-1H-inden-1-amine hydrochloride With tetrabutylammomium bromide; sodium hydroxide In water at 15 - 20℃; for 0.25h; Stage #2: propargyl benzenesulfonate In water at 15 - 20℃; for 2.75h; | 81.0 g |
(R)-N-indan-1-yl-4-nitro-N-prop-2-ynyl-benzenesulfonamide
rasagiline
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol | 64% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 30℃; for 12h; Reflux; | 59.7% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.166667h; Flow reactor; | 58% |
With triethylamine In tetrahydrofuran at 50℃; |
INDANE
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Rh2[(S)-(adamantan-1-yl)(tetrachlorophthalimido)CHCOO]4; PhI(OAc)2 / various solvent(s) / 3 h / 23 °C 2: 75 percent / K2CO3 3: 64 percent / DBU; HSC2H4OH View Scheme |
(R)-N-indan-1-yl-4-nitrobenzenesulfonamide
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / K2CO3 2: 64 percent / DBU; HSC2H4OH View Scheme |
Conditions | Yield |
---|---|
In dichloromethane at -29 - 20℃; | A n/a B n/a |
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene | |
With sodium hydroxide In water at 20℃; |
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 40 - 50℃; pH=14; Product distribution / selectivity; |
R-(-)-N-(2,3 dibromopropyl)-1-aminoindan
rasagiline
Conditions | Yield |
---|---|
With potassium hydroxide In denaturated industrial spirit; water at 80 - 90℃; for 5h; |
Conditions | Yield |
---|---|
Stage #1: (R)-1-Aminoindane With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 5℃; Stage #2: propargyl p-toluenesulfonate In tetrahydrofuran at 0 - 25℃; Stage #3: With sodium hydroxide In water for 0.25h; | |
Stage #1: (R)-1-Aminoindane With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 5℃; Stage #2: propargyl p-toluenesulfonate In tetrahydrofuran at 15 - 20℃; |
2,3-dihydro-1H-inden-1-amine
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide / toluene; water / 4.95 h / 20 - 47 °C / Inert atmosphere; Industry scale 2: isopropyl alcohol; water / 25 °C / Reflux; Inert atmosphere; Industry scale; Resolution of racemate 3: sodium hydroxide / toluene; water / 40 - 47 °C / Industry scale; Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2: 0.75 h / 25 - 65 °C 3: sodium hydroxide / water / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 2: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 3: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux View Scheme | |
Multi-step reaction with 5 steps 1: ethanol; tert-butyl methyl ether / 20 °C 2: ethanol / 2.32 h / 79 °C 3: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 4: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 5: sodium hydroxide / toluene / 29 h / 30 °C View Scheme |
rasagiline
Conditions | Yield |
---|---|
With sodium hydroxide In water; toluene at 40 - 47℃; Industry scale; Inert atmosphere; |
inden-1-one
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: toluene-4-sulfonic acid / tert-butyl methyl ether / 8 h 1.2: 1 h / -70 - -30 °C 2.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -70 - -30 °C 2.2: 1 h / 20 °C 3.1: tert-butyl methyl ether / 21 h / 10 °C / Heating 4.1: sodium hydroxide View Scheme | |
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride; sodium hydroxide / water; methanol / 70 - 75 °C 2: hydrogen; ammonia / Raney nickel / methanol / 10 - 42 °C / Autoclave 3: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 4: 0.75 h / 25 - 65 °C 5: sodium hydroxide / water / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: hydroxylamine hydrochloride / ethanol; water / 0.75 h / Reflux 2: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 70 °C 3: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 4: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 5: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux View Scheme |
N-(2,3-dihydroinden-1-ylidene)prop-2-yn-1-amine
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -70 - -30 °C 1.2: 1 h / 20 °C 2.1: tert-butyl methyl ether / 21 h / 10 °C / Heating 3.1: sodium hydroxide View Scheme |
N-trifluoroacetyl-(R)-1-aminoindan
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 0.17 h / 30 - 35 °C 1.2: 4 h / 30 - 35 °C 2.1: potassium hydroxide / water; methanol / 30 - 35 °C View Scheme | |
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile; toluene / 30 - 35 °C 2: potassium hydroxide; water / methanol / 0.5 h / 30 - 35 °C View Scheme |
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 0.58 h / 20 °C / Ice bath 2.1: caesium carbonate / acetonitrile / 0.17 h / 30 - 35 °C 2.2: 4 h / 30 - 35 °C 3.1: potassium hydroxide / water; methanol / 30 - 35 °C View Scheme |
C14H12F3NO
rasagiline
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 30 - 35℃; | |
With water; potassium hydroxide In methanol at 30 - 35℃; for 0.5h; | 14.3 g |
N-propargyl-1-aminoindan
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.75 h / 25 - 65 °C 2: sodium hydroxide / water / 20 °C View Scheme |
indan-1-one oxime
rasagiline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogen; ammonia / Raney nickel / methanol / 10 - 42 °C / Autoclave 2: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 3: 0.75 h / 25 - 65 °C 4: sodium hydroxide / water / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 70 °C 2: Candida antarctica lipase B; Pd/AlO(OH); potassium carbonate / toluene / 12 h / 50 °C / Resolution of racemate; Inert atmosphere; Schlenk technique; Enzymatic reaction 3: triethanolamine; sodium hydroxide / water / 6.25 h / 80 °C / Reflux 4: potassium carbonate / acetonitrile / 12 h / 30 °C / Reflux View Scheme | |
Multi-step reaction with 6 steps 1: ammonia; hydrogen / methanol / 20 h / 42 °C / 2625.26 Torr 2: ethanol; tert-butyl methyl ether / 20 °C 3: ethanol / 2.32 h / 79 °C 4: sodium hydroxide / ethyl acetate / 0.5 h / 20 °C 5: hydrogenchloride / isopropyl alcohol / 0.5 h / 5 - 20 °C / Inert atmosphere 6: sodium hydroxide / toluene / 29 h / 30 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: (R)-2,3-dihydro-1H-inden-1-amine hydrochloride With potassium carbonate In acetonitrile at 60 - 62℃; for 1h; Stage #2: propargyl bromide In acetonitrile for 28h; Concentration; Time; | 22 g |
Conditions | Yield |
---|---|
With Chiralcel-OJ-H (4-methylbenzoate cellulose coated on silica) column In ethanol; hexane; diethylamine; isopropyl alcohol at 27℃; Temperature; Solvent; Resolution of racemate; |
Conditions | Yield |
---|---|
In ethanol; water for 2h; Product distribution / selectivity; | 100% |
In water; isopropyl alcohol at 40℃; for 1h; |
Conditions | Yield |
---|---|
In acetone for 2h; | 100% |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; | 100% |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; | 100% |
Conditions | Yield |
---|---|
In acetone for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: sodium docusate With hydrogenchloride In dichloromethane; water Stage #2: rasagiline In acetone for 2h; Product distribution / selectivity; | 100% |
Conditions | Yield |
---|---|
In acetone | 100% |
In isopropyl alcohol at 20℃; Cooling with ice; | 63% |
sodium 4-dodecylbenzenesulfonate
rasagiline
rasagiline 4-dodecylbenzenesulfonate
Conditions | Yield |
---|---|
With acetic acid In water; acetone for 2h; | 100% |
benzenesulfonic acid
rasagiline
R-(+)-N-propargyl-1-aminoindan besylate
Conditions | Yield |
---|---|
In toluene at 20℃; Product distribution / selectivity; | 99.5% |
In ethyl acetate at 10 - 25℃; for 3h; Product distribution / selectivity; |
rasagiline
[14C]-Rasagiline hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In tert-butyl methyl ether at 10 - 15℃; for 0.5h; Product distribution / selectivity; | 99% |
With hydrogenchloride In diethyl ether Product distribution / selectivity; Cooling with ice; | |
With hydrogenchloride In water; isopropyl alcohol at 40℃; for 2h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; Product distribution / selectivity; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In tert-butyl methyl ether at 5 - 10℃; for 0.5h; Solvent; Acidic conditions; | 99% |
Conditions | Yield |
---|---|
In isopropyl alcohol for 1h; Reflux; | 98% |
In toluene; acetonitrile at 40 - 80℃; Product distribution / selectivity; | 86.2% |
In isopropyl alcohol at 5 - 10℃; for 0.5h; | 83% |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
In di-isopropyl ether for 1.5h; Product distribution / selectivity; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
In isopropyl alcohol | 93.1% |
rasagiline
(1R)-2,3-dihydro-N-2-propynyl-1H-indane-1-amine hydrobromide
Conditions | Yield |
---|---|
With hydrogen bromide In isopropyl alcohol at 5 - 10℃; for 0.5h; | 90% |
With hydrogen bromide at 25 - 65℃; for 0.5h; Product distribution / selectivity; |
hydrogen bromide
rasagiline
(1R)-2,3-dihydro-N-2-propynyl-1H-indane-1-amine hydrobromide
Conditions | Yield |
---|---|
In isopropyl alcohol at 5 - 10℃; for 0.5h; | 90% |
L-Tartaric acid
rasagiline
Conditions | Yield |
---|---|
In isopropyl alcohol at 40℃; for 2.16667h; | 88% |
In methanol; butanone for 1.16667h; Solvent; Time; Temperature; Reflux; | 72% |
In isopropyl alcohol at 40℃; for 2h; Product distribution / selectivity; |
naphthalene-1,5-disulfonate
rasagiline
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Cooling with ice; | 86% |
(S)-Mandelic acid
rasagiline
R-(+)-N-propargyl-1-aminoindane L-(+)-mandelate
Conditions | Yield |
---|---|
In isopropyl alcohol at 20℃; Heating; Cooling with ice; | 85% |
In n-heptane; isopropyl alcohol | |
In ethyl acetate; isopropyl alcohol at 20℃; for 24h; Heating; |
1-hexadecylcarboxylic acid
rasagiline
(1R)-2,3-dihydro-N-2-propynyl-1H-indane-1-amine palmitate
Conditions | Yield |
---|---|
In isopropyl alcohol at 5 - 10℃; for 0.5h; | 85% |
In isopropyl alcohol at 5 - 10℃; for 0.5h; | 85% |
Conditions | Yield |
---|---|
In isopropyl alcohol Heating; Cooling with ice; | 84% |
(1S)-10-camphorsulfonic acid
rasagiline
rasagiline (1S)-(+)-10-camphorsulfonate
Conditions | Yield |
---|---|
In methanol at 20℃; for 1h; | 79% |
In n-heptane; isopropyl alcohol |
The 1H-Inden-1-amine,2,3-dihydro-N-2-propyn-1-yl-, (1R)- is an organic compound with the formula C12H13N. The IUPAC name of this chemical is (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine. With the CAS registry number 136236-51-6, it is also named as (R)-2,3-Dihydro-N-2-propynyl-1H-inden-1-amine. The product's classification codes are Central Nervous System Agents; Enzyme Inhibitors; Monoamine Oxidase Inhibitors; Neuroprotective Agents; Protective Agents.
Physical properties about 1H-Inden-1-amine,2,3-dihydro-N-2-propyn-1-yl-, (1R)- are: (1)ACD/LogP: 2.27; (2)ACD/LogD (pH 5.5): 0.31; (3)ACD/LogD (pH 7.4): 1.92; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 14.07; (6)ACD/KOC (pH 5.5): 4.48; (7)ACD/KOC (pH 7.4): 183.99; (8)#H bond acceptors: 1; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 3.24 Å2; (12)Index of Refraction: 1.576; (13)Molar Refractivity: 53.91 cm3; (14)Molar Volume: 162.7 cm3; (15)Polarizability: 21.37×10-24cm3; (16)Surface Tension: 43.6 dyne/cm; (17)Density: 1.05 g/cm3; (18)Flash Point: 146.8 °C; (19)Enthalpy of Vaporization: 54.6 kJ/mol; (20)Boiling Point: 305.5 °C at 760 mmHg; (21)Vapour Pressure: 0.000816 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: C#CCN[C@H]2c1ccccc1CC2
(2)InChI: InChI=1/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1
(3)InChIKey: RUOKEQAAGRXIBM-GFCCVEGCBG
(4)Std. InChI: InChI=1S/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2/t12-/m1/s1
(5)Std. InChIKey: RUOKEQAAGRXIBM-GFCCVEGCSA-N
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