Benzaldehyde → 1-Benzylidene-pyrrolidinium chloride

HRID 9005Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([Cl:17])(=O)C>>[Cl-:17].[CH:6](=[N+:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 6367Acetyl chloride

HCID 31268Pyrrolidine

Product 1

HCID 109323601-Benzylidene-pyrrolidinium chloride

Procedure

The reaction of 16.4 ml (0.200 mol) pyrrolidine and 10.1 ml (0.100 mol) benzaldehyde in accordance with general synthesis instructions 2 and subsequent reaction with 6.0 ml (0.100 mol) acetyl chloride in accordance with general synthesis instructions 3 gave 14.1 g (corresponding to 72% of the yield calculated by theory) 1-benzylidene-pyrrolidinium chloride.

Workup

customwith general synthesis instructions 3

Sources & evidence

ORD record: ord-55eedef74ef9485e918bed4ebdb783d6
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091220B2

Reaction notes

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