Benzenesulfonyl chloride → HCID 1438176, compound

HRID 1614599Notes

Reaction equation

HRID 1614599 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 g, 0.219 mol) and benzenesulfonyl chloride (44 g, 0.25 mol) in 500 mL of pyridine was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was extracted with dilute H2SO4 and then dried (MgSO4). The volume was reduced to 400 mL, hexane was added, and 39.20 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 CH2Cl2 and dilute NaOH
  3. extractionThe CH2Cl2 solution was extracted with dilute H2SO4
  4. dry with materialdried (MgSO4)
  5. additionwas added
  6. custom39.20 g (50.6%) of the title compound was collected as a white crystalline solid, mp 156.5°-158° C.

Sources & evidence

ORD record
ord-eaf6ef151d494a2b89740dcb44182486
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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