1-Chloroethyl chloroformate → 4-(4-Chlorophenyl)tetrahydropyridine

HRID 242545Notes

Reaction equation

HRID 242545 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(C)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>C(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:11]2[CH:10]=[CH:9][NH:8][CH2:13][CH2:12]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18675725HCID 18675725, compound

Product 1

HCID 4173784-(4-Chlorophenyl)tetrahydropyridineYield 125.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of N-benzyl-4-(4-chlorophenyl)-4-methylpiperidine (3) (0.41 g, 1.4 mmol) in CH2Cl2 was 1.1 equivalent of 1-chloroethylchloroformate. The reaction was then heated to reflux for 2 hrs. Excess solvent was removed and the residue was brought up into methanol. The mixture was refluxed for 2 hrs and excess methanol was removed under reduced pressure. Precipitation of the hydrochloride salt 4 by the addition of CH2Cl2 followed by filtration resulted in the quantitative isolation of the desired crystalline product 4 (100%, 0.34 g). MS m/z: (M+210)

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 2 hrs
  3. customExcess solvent was removed
  4. temperatureThe mixture was refluxed for 2 hrs
  5. customexcess methanol was removed under reduced pressure
  6. customPrecipitation of the hydrochloride salt 4
  7. additionby the addition of CH2Cl2
  8. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-3e60337677544041ac0ee8b0ea12d91a
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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