Lithium Hydroxide → Succinanilic acid

Participants

Reaction Steps

The synthesis of the succinamide analogs 29, 30, 31, 32, and 33 are described in Schemes 12, 13, and 14. N-Phenyl-succinamic acid was prepared via a two step reaction sequence analogous to the preparation of the N-phenyl-malonamic acid: 1) reaction of aniline with methyl 4-chloro-3-oxobutyrate followed by 2) treatment with lithium hydroxide. Coupling of N-phenyl-succinamic acid with 1-(2-methylamino-(S)-2-phenyl-ethyl)-pyrrolidin-(S)-3-ol, 1-(3-methyl-(S)-2-methylamino-butyl)-pyrrolidin-(S)-3-ol or 1-piperidin-(S)-2-ylmethyl-pyrrolidin-(S)-3-ol afforded 29, 30 and 31, respectively.

Provenance & Evidence