Benzenesulfonyl chloride → HCID 1438176, compound

HRID 1460230Notes

Reaction equation

HRID 1460230 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([S:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:25])=[O:24])[CH2:11][CH2:10]2)=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 3084438p-Fluorophenyl 4-piperidyl ketone hydrochloride

Product 1

HCID 1438176HCID 1438176, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine hydrochloride (53.3, 0.219 mole and benzenesulfonyl chloride (44 g, 0.25 mole) in 500 ml of pyridine was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was extracted with dilute sulfuric acid and then was dried over magnesium sulfate. The volume was reduced to 400 ml, hexane was added and 39.2 g (50.6%) of the title compound was collected as a white, crystalline solid, mp 156.5°-158° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. extractionThe methylene chloride solution was extracted with dilute sulfuric acid
  4. dry with materialwas dried over magnesium sulfate
  5. additionwas added
  6. custom39.2 g (50.6%) of the title compound was collected as a white, crystalline solid, mp 156.5°-158° C.

Sources & evidence

ORD record
ord-5afd374d3a56452782216b23e9dc9af3
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

Loading…