1-Chloroethyl chloroformate → 4-Propenylidenepiperidine hydrochloride

HRID 861948Notes

Reaction equation

HRID 861948 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[CH:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:17]C(OC(Cl)C)=O>ClC(Cl)C>[ClH:17].[CH:14](=[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 149666551-Benzyl-4-propylidenepiperidine

Product 1

HCID 867520404-Propenylidenepiperidine hydrochlorideYield 110.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

There was dissolved 4.5 g (21 mmol) of 1-benzyl-4-propylidenepiperidine in 20 ml of dichloroethane and thereto 2.8 ml (25 mmol) of 1-chloroethyl chloroformate was added dropwise under cooling with ice. The reaction solution was stirred at room temperature for 30 minutes and then refluxed with heating for 30 minutes. The reaction solution was concentrated to 10 ml by removing the solvent under reduced pressure, and thereto was added 60 ml of methanol and the obtained mixture was refluxed with heating for 12 hours. The solvent was removed under reduced pressure to obtain 3.7 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. temperaturerefluxed
  3. temperaturewith heating for 30 minutes
  4. concentrationThe reaction solution was concentrated to 10 ml
  5. customby removing the solvent under reduced pressure
  6. additionwas added 60 ml of methanol
  7. temperaturethe obtained mixture was refluxed
  8. temperaturewith heating for 12 hours
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c4cc18d6c77743f2bbfb66d9088d7a7c
Source dataset
uspto-grants-1998_02
Patent number
US05716969

Reaction notes

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