N-(4-{[3-(morpholin-4-yl)propyl]sulfamoyl}phenyl)acetamide → 4-amino-N-[3-(morpholin-4-yl)propyl]benzene-1-sulfonamide

HRID 215756Notes

Reaction equation

HRID 215756 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C>C(Cl)(Cl)Cl>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][CH2:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 2144799N-(4-{[3-(morpholin-4-yl)propyl]sulfamoyl}phenyl)acetamide

Product 1

HCID 49628214-amino-N-[3-(morpholin-4-yl)propyl]benzene-1-sulfonamideYield 701.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The mixture of 3.4 g (0.001 mol) of 4-acetamido-N-(3-morpholinopropyl)benzene sulphonamide XIII and 4 ml of 17% acid was heated for 3.5 hours until slight boiling under stirring. The mixture was cooled to the room temperature and neutralized to chloroform. The solvent was distilled off from the solution and the distillation residue-oil was macerated with ether. Afforded 2.1 g of (71%) 4-amino-N-(3-morpholinopropyl)benzenesulphonamide XIV. Colourless solid, m.p. 96-97° C. Lit. [8] reports 95° C.

Workup

  1. temperaturewas heated for 3.5 hours until slight boiling
  2. distillationThe solvent was distilled off from the solution
  3. distillationthe distillation residue-oil

Sources & evidence

ORD record
ord-cc1d299921224b4da6ce8c4a34d72e91
Source dataset
uspto-grants-2012_06
Patent number
US08193184B2

Reaction notes

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