Carbamoyl-3-arolpyrrolidine und Verfahren zu deren Herstellung

1,267,583. 1 - Carbamoyl - 3 - aroylpyrrolidines. A. H. ROBINS CO. Inc. 18 June, 1969 [20 June, 1968], No. 30873/69. Heading C2C. Novel compounds of the formula where R1 and R2 each denote H, C 1-8 alkyl, C 3-9 cycloalkyl or aryl, and R3 denotes H, F, Cl, Br, CF 3 or C 1-8 alkyl, and acid addition salts thereof, may be obtained by the steps: (1) reacting a 1 - benzyl - 3 - cyano - pyrrolidine with Aryl- Mg-X (where X = Cl or Br) to yielda 1-benzyl-3- aroylpyrrolidine, (2) reacting the product with CNBr to form a 1-cyano-3-aroylpyrrolidine, (3) refluxing the latter with 4N HCl to yield a 1- carbamoyl-3-aroylpyrrolidine, and optionally (4) hydrolysing the product of (3) by prolonged refluxing with conc. HCl to form a 3-aroylpyrrolidine, and (5) reacting the product with a C 1-8 alkyl isocyanate, aryl isocyanate, N-C 3-9 cycloalkyl-N-aryl carbamoyl halides, N,N-di- C 1-8 alkyl carbamoyl halide or N,N-diaryl carbamoyl halide. The compounds have anticonvulsant activity. N-R1,N-R2-Carbamoyl chlorides are obtained by reacting the corresponding amine R1R2NH with phosgene.