3,4-Dichlorobenzyl chloride → 3,4-dichlorobenzyl-4-piperidone

HRID 1070488Notes

Reaction equation

HRID 1070488 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5]Cl.O.Cl.[O:13]=[C:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][N:17]1[CH2:18][CH2:19][C:14](=[O:13])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 8471TriethylamineHCID 2723901Piperonylamine

Product 1

HCID 108487763,4-dichlorobenzyl-4-piperidone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-dichlorobenzyl chloride (2.8 ml), 4-ketopiperidine hydrochloride monohydrate and triethylamine (8 ml) in dimethylformamide (30 ml) was stirred at room temperature for 20 h. The mixture was partitioned between water and ethyl acetate, the organic layer dried and evaporated under reduced pressure. Purification was by chromatography eluting with 40-50% ethyl acetate/isohexane. Yield 2.1 g.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customthe organic layer dried
  3. customevaporated under reduced pressure
  4. customPurification
  5. washeluting with 40-50% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-659355a251114a28b73fe0c6bc1705bb
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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