Phenibut synthesis

10synthesis methods

Product Name:Phenibut
CAS Number:1078-21-3
Molecular formula:C10H13NO2
Molecular Weight:179.22

Phenibut was synthesized by Perekalin and his associates at the Department of Organic Chemistry of the Herzen Pedagogic Institute in St. Petersburg, the Russian Federation. In initial publications phenibut was known as phenigamma (Lapin, 2001, V. V. Perekalin, 1954).
Fenibut synthesis: from benzoyl chloride and ethyl acetoacetate as raw materials, through condensation and hydrolysis of ethyl benzoyl acetate, and then condensation of benzaldehyde and nitromethane to generate trans-nitrostyrene, and then the two are combined. Micheal addition, the adduct is then catalytically hydrogenated with Raney nickel, and finally hydrolyzed in concentrated hydrochloric acid to produce phenibate.

Synthesis of Phenibut (16) and Baclofen (17).

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Yield:-

Reaction Conditions:

with hydrogenchloride at 10;Reflux;

Steps:

2.2.1.6. Synthesis of Amino-3-phenylbutanoic acid (7)

The solution of Phenylpyrrolidin-2-one (6) (80 mg, 0.55mmol)watirredinHCl(6N)underrefluxat1°Cfor241H NMR (300 MHz, D2O) d 2.65 (dd, 1H, J 15.8 and 8.8Hz), 2.75 (dd, 1H, J 15.8 and 5.3 Hz), 3.10-3.30 (m, 3H),7.26-7.36 (m, 5H); 13C NMR (75 MHz, D2O) d 40.7, 42.4,46.3, 130.3, 130.8, 131.8, 140.8, 177.9. IR (KBr film, cm-1): = 3317-2567, 1711, 1590, 1515, 1485, 1402, 1259, 1199,1146, 972, 860, 761, 701.

References:

Keniche, Assia;El Ouar, Ibtissem;Zeghina, Ibtissem;Dib, Mohammed El Amine [Combinatorial Chemistry and High Throughput Screening,2022,vol. 25,# 1,p. 187 - 196]