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PROCESSES FOR SYNTHESIZING N-(CARBAMOYLMETHYL-4-PHENYL-2-PYRROLIDINONE AND INTERMEDIATES THEREOF

IP.com Disclosure Number: IPCOM000211198D
Publication Date: 2011-Sep-27
Document File: 3 page(s) / 23K

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The IP.com Prior Art Database

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PROCESSES FOR SYNTHESIZING N-(CARBAMOYLMETHYL-4- PHENYL-2-PYRROLIDINONE AND INTERMEDIATES THEREOF

     N-(Carbamoylmethyl-4-phenyl-2-pyrrolidinone, referred to as 'Compound 1', has the following formula:

N

NH2

O

O

(1)

Described hereinafter, is a process for the preparation of N-

(Carbamoylmethyl-4-phenyl-2-pyrrolidinone.

The process can be illustrated by the following scheme:

O

NH2

X

O

O R2

NH2

    O O

O

O

+

base/solvent

N

N

R2

I(a)

O

O

R1

I

II

III

X=halogen

hydrogenation

NH2

O

N

O

N-(Carbamoylmethyl-4-phenyl-2-pyrrolidinone

The above process comprises:

a) Condension of alkyl/aryl ester of glycine of formula I(a) or its pharmaceutically acceptable salts, to compound of formula (I) in presence of base and solvent to produce compound of formula (II);

b) Amidation of compound of formula (II), obtained from step (a) to produce

compound of formula (III);

c) Hydrogenation of compound of formula (III) in presence of hydrogenating agent to obtain N-(Carbamoylmethyl-4-phenyl-2-pyrrolidinone. 1


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Step (a), can be optionally done in the presence base and solvent at ambient temperature.

An ambient temperature for above reaction may be defined as, temperature, on which reactant may completely converted into product.

The base used in step (a) may be selected from organic and inorganic bases. Organic bases may be selected from amines, amines may be optionally substituted aliphatic or aromatic amines or alike. Inorganic bases may be selected from alkali or alkaline metal hydroxides, carbonates and bicarbonates. The solvents used in step (a) may be selected from polar protic or aprotic solvents. Polar protic or aprotic solvents may be selected from optionally substituted or branched aliphatic or aromatic ketones, optionally substituted or branched cyclic aliphatic or aromatic ethers, optionally substituted or branched aliphatic or aromatic nitriles, optionally substituted or branched aliphatic or aromatic amides or alike. R1 and R2 may be selected from optionally substituted or branched alkyl or aryl group. The said process produces, comp...