Ethanol → Ethyl 3-benzylamino-4-piperidino-5-sulphamyl-benzoate

Participants

Reaction Steps

A mixture of 3-amino-4-piperidino-5-sulphamyl-benzoic acid (2.5 g), benzyl bromide (1.4 g), and dry ethanol (30 ml) was refluxed for 3 days. The reaction mixture was evaporated in vacuo, and the residue was washed with petroleum ether. The crude ethyl 3-benzylamino-4-piperidino-5-sulphamyl-benzoate obtained was saponified by addition of 1N sodium hydroxide and heated on a steam bath for 1 hour. After cooling and adjusting the pH to 4 by means of a 4N hydrochloric acid, 3-benzylamino-4-piperidino-5-sulphamyl-benzoic acid precipitated. After collecting and recrystallizing from aqueous ethanol, the compound was obtained as a hemi-hydrate with a melting point of 195° C.

Provenance & Evidence