Potassium Carbonate → Rasagiline

HRID 401851Notes

Reaction equation

HRID 401851 reaction equation
[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1.Cl.C(Cl)C#C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]#[C:2][CH2:3][NH:4][C@H:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 9794292136236-50-5

Product 1

HCID 3052776RasagilineYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Another process for preparation of Rasagiline hydrochloride as disclosed in EP '492 comprises reaction of R(−)-1-aminoindan (8) with propargyl chloride (6) in presence of potassium carbonate in acetonitrile (ACN) at 60° C. for 16 hours to obtain R(+) Rasagiline base (9) which is then purified by column chromatography. The purified base is then converted to R(+)-Rasagiline hydrochloride followed by recrystallization with isopropanol. The main disadvantage of this process is longer reaction time (16 hours) and low overall yield of about 56%.

Sources & evidence

ORD record
ord-07d03e85e0ac476bb65c4f60769aa0a2
Source dataset
uspto-grants-2014_06
Patent number
US08741962B2

Reaction notes

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