GB1157638A - Aminonitrile Derivatives and Process for their Preparation - Google Patents

Abstract

1,157,638. Aminonitrile derivatives and their preparation. STERLING DRUG Inc. 1 July, 1966 [1 July, 1965], No. 1746/69. Divided out of 1,157,637. Heading C2C. Compounds of the formulae may be obtained by reductively alkylating 2- methylglutaronitrile in the presence of an amine, HNR 1 R 2 , where NR 1 R 2 is a tertiary amino group and R 1 and R 2 are the same or different and represent lower or higher alkyl, hydroxy lower or higher alkyl, lower alkoxy higher or lower alkyl, di-lower alkylamino lower or higher alkyl, C3<SP>_</SP>7 cycloalkyl, phenyl or substituted phenyl, said substitutents being hydroxy, lower alkoxy, di-lower alkyl amino, trifluoro methyl, lower alkyl mercapto or halo, or R 1 and R 2 taken together form a heterocyclic ring containing at least one heteroatom, the terms " lower and " higher " denoting C 1-8 and C 8-18 respectively. The 2-methyl glutaronitrile may be prepared in a first stage by reducing 2- methylene glutaronitrile at 60-80‹ C. under a pressure of 100-200 p.s.i. hydrogen in the presence of a catalyst such as palladium, platinum, Raney cobalt or Raney nickel which may be supported on a carrier such as carbon, barium sulphate, strontium carbonate, calcium carbonate or alumina. The reductive alkylation step is preferably effected at 90-110‹ C. under a hydrogen pressure of 100-500 p.s.i. employing the same catalyst as in the above first stage. Example 3 also illustrates the preparation of a compound of the Formula I by alkylation of the corresponding free amine.