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Basic Information

Molecular Structure:
CAS No.:	161735-79-1
Name:	Rasagiline mesylate
Article Data:	22

Formula:	C₁₂H₁₃N^.CH₄O₃S
Molecular Weight:	267.349
Synonyms:	R-(+)-Rasagiline mesylate;methanesulfonic acid; (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine;Rasagiline methanesulfonate;1H-Inden-1-amine, 2,3-dihydro-N-2-propynyl-, (R)-, methanesulfonate;(R)-N-2-Propynyl-1-indanamine methanesulfonate;(R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine methanesulfonate;
EINECS:	694-423-3
Density:	1.05 g/cm3
Melting Point:	155-158 °C
Boiling Point:	305.5 °C at 760 mmHg
Flash Point:	146.8 °C
Appearance:	white to off-white crystalline solid
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	24/25
PSA:	74.78000
LogP:	2.87240

Synthetic route

: 75-75-2
methanesulfonic acid

: 136236-51-6
rasagiline

: 161735-79-1
rasagiline mesylate

Conditions

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%

: 75-75-2
methanesulfonic acid

: (1R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine hemihydrate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Stage #1: (1R)-N-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-amine hemihydrate With potassium carbonate In water pH=Ca. 10; Large scale; Stage #2: methanesulfonic acid In isopropyl alcohol at 20℃; for 1.5h; Large scale;	92.6%

: 75-75-2
methanesulfonic acid

: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Stage #1: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate With sodium hydrogencarbonate In water; ethyl acetate at 20 - 25℃; Inert atmosphere; Stage #2: methanesulfonic acid In isopropyl alcohol Reflux;	89%

: 75-75-2
methanesulfonic acid

: rasagiline tartrate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
In isopropyl alcohol at 5℃; for 1.5h; Reflux;	83%

: 75-75-2
methanesulfonic acid

: rasagiline tartrate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
In isopropyl alcohol at 5 - 10℃; for 0.75h;	83%

: 75-75-2
methanesulfonic acid

: 1166392-46-6
N-(2,3 dibromopropyl)-1-aminoindan

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Stage #1: N-(2,3 dibromopropyl)-1-aminoindan With potassium hydroxide In denaturated industrial spirit; water at 80 - 90℃; for 5h; Stage #2: methanesulfonic acid In isopropyl alcohol at 25 - 30℃;

: 75-75-2
methanesulfonic acid

: (R-(+)-N-propargyl-1-aminoindan)L-tartarate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
In acetone for 0.75h; Product distribution / selectivity; Reflux;	n/a

: 34698-41-4
2,3-dihydro-1H-inden-1-amine

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 24 h / 55 °C 2.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 3.1: ammonia / water / pH ~ 8.5 - 9 3.2: 2 h / 25 - 30 °C View Scheme
Multi-step reaction with 4 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 4: acetone / 1 h / 25 - 35 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide / 7 h / 40 - 70 °C 2.1: 0.75 h / 25 - 65 °C 3.1: sodium hydroxide / water / 20 °C 4.1: hydrogen bromide / 0.5 h / 25 - 65 °C 5.1: sodium hydroxide / ethyl acetate / 4 h / 65 °C 5.2: 0.5 h / 40 °C View Scheme
Multi-step reaction with 4 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 4: isopropyl alcohol / 0.5 h / 5 - 10 °C View Scheme
Multi-step reaction with 6 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 6: isopropyl alcohol / 1 h / 55 - 80 °C View Scheme

: 75-75-2
methanesulfonic acid

: 1201685-18-8
(1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Stage #1: (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine L-(+)-tartrate With ammonia In water pH=~ 8.5 - 9; Stage #2: methanesulfonic acid In acetone at 25 - 30℃; for 2h; Product distribution / selectivity;

: 83-33-0
inden-1-one

: 161735-79-1
rasagiline mesylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethanol / 8 h / 25 - 30 °C 2.1: ethanol; sodium tetrahydroborate / 8 h / 25 - 30 °C 3.1: isopropyl alcohol / 1.5 h / 25 - 30 °C / Reflux 4.1: ammonia / water / pH ~ 8.5 - 9 4.2: 2 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 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 5.1: isopropyl alcohol / 16 h / 20 - 75 °C View Scheme
Multi-step reaction with 6 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 6: acetone / 1 h / 25 - 35 °C View Scheme

Raw Materials

75-75-2

83-33-0

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Chemistry

Product Name: Rasagiline Mesylate (CAS NO.161735-79-1)

IUPAC Name: methanesulfonic acid; (1R)-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine
Molecular Formula: C₁₃H₁₇NO₃S
Molecular Weight: 267.343980 g/mol
Appearance: White to Off-White Crystalline Solid
Density: 1.05 g/cm³
Boiling Point: 305.5 °C at 760 mmHg
Flash Point: 146.8 °C
Categories: APIs; Chiral; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Rasagiline

Uses

Rasagiline Mesylate (CAS NO.161735-79-1) is a selective irreversible MAO-B inhibitor.

Specification

Rasagiline Mesylate , its CAS NO. is 161735-79-1, the synonyms are (r)-n-2-Propynyl-1-indanamine methanesulfonate ; (1R)-2,3-Dihydro-N-2-propyn-1-yl-1H-inden-1-amine Mesylate ; (R)-N-2-Propynyl-1-indanamine Mesylate ; Agilect ; Azilect ; TVP-101 ; Rasagiline nesylate .