3-Phenylpiperidine hydrochloride → 3-Cyclohexylpiperidine

HRID 130781Notes

Reaction equation

HRID 130781 reaction equation
Cl.[C:2]1([CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Rh]>[CH:2]1([CH:8]2[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 173900083-Phenylpiperidine hydrochloride

Product 1

HCID 38093533-Cyclohexylpiperidine

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

Combine 3-phenyl-piperidine hydrochloride (0.206 g, 1.04 mmol) and 5% rhodium on alumina (0.112 g, 0.0544 mmol) in methanol (50 mL) and stir at 50° C. at a H2 pressure of 60 psi. After 4 d, purify the reaction mixture by ion exchange chromatography (SCX resin, methanol→2 M ammonia/methanol) to provide 0.164 g (3:1 mixture of product:starting material) which was used in the next step without further purification: mass spectrum (electrospray): m/z=168.1 (M+1−product), 162.1 (M+1−starting material).

Workup

  1. custompurify the reaction mixture by ion exchange chromatography (SCX resin, methanol→2 M ammonia/methanol)
  2. customto provide
  3. addition0.164 g (3:1 mixture of product:starting material) which
  4. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2eca5b25da214c409b04abc327f657fa
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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