Acetyl chloride → 1-(2-Methyl-benzylidene)-piperidinium chloride

HRID 1835772Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O.[C:16](Cl)(=O)C>>[Cl-:7].[CH3:10][C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[CH:16]=[N+:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 69962-Chlorobenzaldehyde

HCID 8082Piperidine

Product 1

HCID 179122571-(2-Methyl-benzylidene)-piperidinium chloride

Procedure

The reaction of 8.5 g (0.100 mol) piperidine and 7.0 g (0.050 mol) 2-chlorobenzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 3.9 g (0.050 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 7.1 g (corresponding to 58% of the yield calculated by theory) 1-(2-methyl-benzylidene)-piperidinium chloride.

Workup

customwith general synthesis instructions 3

Sources & evidence

ORD record: ord-74bed366d59c42c6bbc2d7a3f39b0ceb
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774136B2

Reaction notes

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