Phosgene → 1-(Chloromethylidene)piperidin-1-ium chloride

HRID 1589250Notes

Reaction equation

HRID 1589250 reaction equation
C([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)=O.[C:9]([Cl:12])([Cl:11])=O>C(OCC)C>[Cl-:11].[Cl:12][CH:9]=[N+:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 174291-Piperidinecarboxaldehyde

Product 1

HCID 131802471-(Chloromethylidene)piperidin-1-ium chlorideYield 94.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under dry nitrogen a solution of N-formyl piperidine (170 gm, 1.50 mol) in anhydrous diethyl ether (1.5 L), stirring rapidly at 5° C., is treated with gaseous phosgene (142 gm, 1.44 mol) over the course of 1.5 hours. Ice bath cooling is applied to maintain a temperature of less than 12° C. The resulting while solid is filtered off under dry nitrogen, in vacuum, to give 94.4% (228 gm, 1.36 mol) of N-(chloromethylene)-piperidinium chloride.

Workup

  1. temperatureIce bath cooling
  2. temperatureto maintain a temperature of less than 12° C
  3. filtrationThe resulting while solid is filtered off under dry nitrogen, in vacuum

Sources & evidence

ORD record
ord-c3dae7be4c2c4310b44c60ee9b48e016
Source dataset
uspto-grants-1986_02
Patent number
US04568741

Reaction notes

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