4-Chlorobenzoyl chloride → 4-Chlorobenzaldehyde

HRID 1063356Notes

Reaction equation

HRID 1063356 reaction equation
Cl.BrCCCCOC1CCNCC1.[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl.CCOCC>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 85812949HCID 85812949, compound

Product 1

HCID 77264-Chlorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.4 g (1.47 mmol) 4-(4-Brom-butoxy)-piperidine hydrogen chloride and 0.198 ml (1.54 mmol) 4-chloro-benzoylchloride in 5 ml of CH2Cl2 was added 1 ml (5.87 mmol) of N-ethyldiisopropylamine. The reaction-mixture was stirred for 1 h at RT, diluted with Et2O and then washed with 1N HCl and water. The crude product was purified by chromatography on silica gel with EtOAc/hexane 1:1, to yield 459 mg (84%) of clean 4-(4-Bromo-butoxy)-piperidin-1-yl)-(4-chloro-phenyl)-methanone, MS: 374 (M+).

Workup

  1. washwashed with 1N HCl and water
  2. customThe crude product was purified by chromatography on silica gel with EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-727ead32fda94c6f8438adbb80949fad
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

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