Benzenesulfonyl chloride → HCID 1438176, compound

HRID 1709861Notes

Reaction equation

HRID 1709861 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 (53.30, 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 dried over magnesium sulfate. The volume was reduced to 400 ml, hexane was added and 39.20 g (50.6%) of title compound was collected as a white, crystalline solid, m.p. 156.5°-158°.

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 materialdried over magnesium sulfate
  5. additionwas added
  6. custom39.20 g (50.6%) of title compound was collected as a white, crystalline solid, m.p. 156.5°-158°

Sources & evidence

ORD record
ord-a2ac120294f543d79a4a2fa5671044fd
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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