Potassium Carbonate → Rasagiline

HRID 401850Notes

Reaction equation

HRID 401850 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH2:11](Cl)[C:12]#[CH:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:11]#[C:12][CH2:13][NH:1][C@H:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 123445(+-)-1-Aminoindan

Product 1

HCID 3052776Rasagiline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

EP436492 discloses process for preparation of R-(+)-Rasagiline hydrochloride which involves reaction of racemic 1-aminoindan (2) with propargyl chloride (6) in presence of potassium carbonate in acetonitrile (ACN) at 60° C. for 16 hours to obtain racemic Rasagiline base (4) which is purified using column chromatography. The ethereal solution of purified racemic base is then treated with HCl gas followed by recrystallization using isopropanol (IPA) to obtain racemic Rasagiline hydrochloride (7). R-(+)-Rasagiline is separated from the obtained racemic Rasagiline base (4) by preparative HPLC chromatography and further converted to its hydrochloride salt.

Sources & evidence

ORD record
ord-f079b84aea7242cf95f5a64c9b6dc5f0
Source dataset
uspto-grants-2014_06
Patent number
US08741962B2

Reaction notes

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