1,2-Difluorobenzene → (3,4-Difluorophenyl)(piperidin-4-yl)methanone

HRID 1614617Notes

Reaction equation

HRID 1614617 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C([N:22]1[CH2:30][CH2:29][CH:25]([C:26](Cl)=[O:27])[CH2:24][CH2:23]1)(=O)C.[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38]>>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[O:18])[C:11]2[CH:12]=[CH:13][C:14]([F:17])=[C:15]([F:31])[CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[F:31][C:32]1[CH:37]=[C:36]([CH:35]=[CH:34][C:33]=1[F:38])[C:26]([CH:25]1[CH2:24][CH2:23][NH:22][CH2:30][CH2:29]1)=[O:27]

Participants

5

Reactant 3

HCID 97061,2-DifluorobenzeneHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 1172571-Acetyl-4-(4-fluorobenzoyl)piperidine

Product 2

HCID 14674155(3,4-Difluorophenyl)(piperidin-4-yl)methanoneHCID 19771920HCID 19771920, compound

Procedure

Following the procedure for the preparation of 1-acetyl-4(4-fluorobenzoyl)piperidine (U.S. Pat. No. 3,576,810), 1-acetyl-4(3,4-difluorobenzoyl)piperidine is prepared from 1-acetylisonipecotic acid chloride and 1,2-difluorobenzene. The acetyl group is removed by hydrolysis in dilute hydrochloric acid. Basification followed by extraction with a suitable solvent yields the title compound.

Workup

  1. customThe acetyl group is removed by hydrolysis in dilute hydrochloric acid
  2. extractionBasification followed by extraction with a suitable solvent

Sources & evidence

ORD record
ord-155d9c1cc1e144ee8ae9517ed1295278
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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