Acetic Acid → 4-(4-Fluoro-benzyl)-piperidin-4-ol acetate

HRID 854605Notes

Reaction equation

HRID 854605 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.[C:23](O)(=[O:25])[CH3:24]>C(O)C.[Pd]>[C:23]([O:14][C:11]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)(=[O:25])[CH3:24]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 108280121-Benzyl-4-(4-fluoro-benzyl)-piperidin-4-ol

Product 1

HCID 694266924-(4-Fluoro-benzyl)-piperidin-4-ol acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-4-(4-fluoro-benzyl)-piperidin-4-ol (5.87 g, 19.6 mmol) in ethanol (80 ml) is treated with acetic acid (1 ml) and with 10% Pd on carbon (1 g). The mixture is stirred at RT under an atmosphere of hydrogen for 20 hours. The mixtre is filtered and the filtrate evaporated. The crude product is treated with dichloromethane. The resultant suspension is filtered and the white solid obtained is washed with cold dichloromethane to afford 4-(4-fluoro-benzyl)-piperidin-4-ol acetate [MH]+ 210.1

Workup

  1. filtrationThe mixtre is filtered
  2. customthe filtrate evaporated
  3. additionThe crude product is treated with dichloromethane
  4. filtrationThe resultant suspension is filtered
  5. customthe white solid obtained
  6. washis washed with cold dichloromethane

Sources & evidence

ORD record
ord-8b0391816e4e46d2bdd4ac7b476dd644
Source dataset
uspto-grants-2007_08
Patent number
US07259173B2

Reaction notes

Loading…