1-Benzyl-4-(4-fluoro-benzyl)-piperidin-4-ol → 4-[(4-Fluorophenyl)methyl]piperidin-4-ol

HRID 1955188Notes

Reaction equation

HRID 1955188 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>[Pd].CCO>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 108280121-Benzyl-4-(4-fluoro-benzyl)-piperidin-4-ol

Product 1

HCID 104886244-[(4-Fluorophenyl)methyl]piperidin-4-olYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-4-(4-fluorobenzyl)-4-hydroxypiperidine (520 mg, 1.7 mmol), 5% Pd/C (150 mg) and EtOH (15 mL) was shaken under H2 (30 psi) for 14 h and filtered. The filtrate was evaporated to give 350 mg (98%) of the title compound as a yellowish oil. 1H NMR (CDCl3), 1.45-1.64 (m, 6H), 2.792 (s, 2H), 2.63-2.96 (m, 4H), 6.97-7.02 (m, 2H), 7.14-7.19 (m, 2H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-42475dadaf0646afaaf1e775fd88be38
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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