Hydrochloric Acid → 1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine

HRID 2232932Notes

Reaction equation

HRID 2232932 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.[Pd]>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:22])[F:23])[CH:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223452021-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyridine

Product 1

HCID 223451981-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidineYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyridine (1.45 g) was dissolved in methanol (40 ml). Concentrated hydrochloric acid (0.2 ml) and 50 mg Pd/C, were added. The resulting mixture was hydrogenated under a hydrogen gas pressure (40 psi) for 1 h and then filtered through a pad of celite. The solvent was evaporated in vacuum and the residue was purified by flash chromatography (SiO2, CH2Cl2:MeOH, 9:1 (v/v)) to give the pure title compound (1.2 g). MS m/z (relative intensity, 70 eV) 353 (M+, 16), 262 (20), 91 (bp), 65 (18), 56 (14).

Workup

  1. customfor 1 h
  2. filtrationfiltered through a pad of celite
  3. customThe solvent was evaporated in vacuum
  4. customthe residue was purified by flash chromatography (SiO2, CH2Cl2:MeOH, 9:1 (v/v))

Sources & evidence

ORD record
ord-362a673cbda6434b830ef4a2e818229d
Source dataset
uspto-grants-2010_05
Patent number
USRE041315E1

Reaction notes

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