Methanol → 4-[4-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)

HRID 856050Notes

Reaction equation

HRID 856050 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:24]C(OCCCl)=O.CO.C(OCC)C>C(Cl)Cl>[ClH:24].[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 123052-Chloroethyl chloroformateHCID 161275071-Benzyl-4-[4-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

Product 1

HCID 215599794-[4-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)Yield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine (2 g, 6.3 mmol) prepared in Reference Example 96 was dissolved in methylene chloride (20 ml), to which 2-chloroethyl chloroformate (1.67 g, 11.68 mmol) was added dropwise under a nitrogen atmosphere while cooling in an ice-bath, and the mixture was stirred at the same temperature for 3 hours. Methanol (20 ml) was added to the mixture, which was heated under reflux for 1 hour. The reaction mixture was allowed to return to room temperature, to which diethyl ether was added, and the resulting precipitates were collected by filtration to afford 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine hydrochloride (1.44 g, yield 87%) as a colorless crystalline powder.

Workup

  1. additionwas added dropwise under a nitrogen atmosphere
  2. temperaturewhile cooling in an ice-bath
  3. temperaturewas heated
  4. temperatureunder reflux for 1 hour
  5. additionwas added
  6. customthe resulting precipitates
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-7d9e55a7c7314b56abe235b75371f0eb
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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