1-Benzylpiperidin-4-yl acetate → Piperidin-4-yl acetate

HRID 1053853Notes

Reaction equation

HRID 1053853 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H][H]>C(O)C.O.[Pd]>[C:1]([O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 119596681-Benzylpiperidin-4-yl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 11252075Piperidin-4-yl acetateYield 92%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10% Pd/C (500 mg) was added to a solution of 1-benzylpiperidin-4-yl acetate [(11 g, 47 mmol), J. Org. Chem. 68(2), 613-616; 2003] in a mixture of ethanol and water (90:10, 110 mL), and the mixture was stirred at 60° C., under 60 psi of hydrogen gas for 18 hours. The reaction mixture was then filtered through Arbocel®, washing through with ethanol, and the filtrate was concentrated in vacuo to afford the title product in 92% yield, 7.2 g. 1H NMR (CDCl3, 400 MHz) δ: 1.60 (m, 2H), 1.81-2.18 (m, 5H), 2.78 (m, 2H), 2.95-3.18 (m, 2H), 4.82 (m, 1H); LRMS APCI+ m/z 145 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered through Arbocel®
  2. washwashing through with ethanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9ab671c75db04f1eb5b525c850cef4bf
Source dataset
uspto-grants-2016_07
Patent number
US09394278B2

Reaction notes

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