1-Chloroethyl chloroformate → 4-Piperidinecarbonitrile hydrochloride

HRID 2300167Notes

Reaction equation

HRID 2300167 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:16]C(OC(Cl)C)=O>ClCCCl>[ClH:16].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 7933831-Benzylpiperidine-4-carbonitrile

Product 1

HCID 227446374-Piperidinecarbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

11.0 g of 1-benzyl-4-piperidinecarbonitrile was dissolved in 100 ml 1,2-dichloroethane, 7.1 ml 1-chloroethyl chloroformate was added thereto under ice-cooling. The mixture was stirred at room temperature for 15 min, and then heated under reflux for 1 hr and 20 min. After evaporating, 50 ml methanol was added thereto and it was heated under reflux for 1 hr. The reaction solution was evaporated, and the crystalline residue was washed with ethyl acetate and collected by filtration to give 8.0 g of 4-piperidinecarbonitrile hydrochloride as white crystals.

Workup

  1. temperatureunder ice-cooling
  2. temperatureheated
  3. temperatureunder reflux for 1 hr and 20 min
  4. customAfter evaporating
  5. addition50 ml methanol was added
  6. temperatureit was heated
  7. temperatureunder reflux for 1 hr
  8. customThe reaction solution was evaporated
  9. washthe crystalline residue was washed with ethyl acetate
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-895e623ba5e940f18d47d244c5c2c093
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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