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

HRID 1287793Notes

Reaction equation

HRID 1287793 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:20])(=[O:19])[NH2:18])[C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([OH:7])=[O:6].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:29](O)[CH3:30]>>[CH2:21]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:17](=[O:19])(=[O:20])[NH2:18])[C:10]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:5]([O:7][CH2:29][CH3:30])=[O:6])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl BromideHCID 215061343-Amino-4-piperidino-5-sulphamyl-benzoic acid

Product 1

HCID 21505995Ethyl 3-benzylamino-4-piperidino-5-sulphamyl-benzoate

Procedure

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.

Workup

  1. temperaturewas refluxed for 3 days
  2. customThe reaction mixture was evaporated in vacuo
  3. washthe residue was washed with petroleum ether

Sources & evidence

ORD record
ord-0460dc7a0397498dae54f61bcfd1d71b
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

Loading…