4-Benzylbenzoate piperidine 4-ethyl benzoate → 4-Ethylbenzoate piperidine-4-benzoic acid

HRID 2190556Notes

Reaction equation

HRID 2190556 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([O-:14])=[O:13])=[CH:10][CH:9]=1)[C:2]1C=CC=CC=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CC[C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][CH:26]=1.[H][H]>CCO.CCOC(C)=O.[Pd]>[CH2:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([O-:14])=[O:13])=[CH:10][CH:9]=1)[CH3:2].[NH:17]1[CH2:22][CH2:21][CH:20]([C:27]2[C:28]([C:31]([OH:33])=[O:32])=[CH:29][CH:30]=[CH:25][CH:26]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 1317300884-Benzylbenzoate piperidine 4-ethyl benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 1317300894-Ethylbenzoate piperidine-4-benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 4-benzylbenzoate-piperidine-4-ethyl benzoate (200 mg, 0.45 mmol) 10% Pd/C (48 mg) in EtOH/EtOAc (1:1) was hydrogenated under 1 atm of hydrogen for 2 h. Then followed addition of additional portion of 10% Pd/C (100 mg) and the mixture was hydrogenated again under 1 atm of hydrogen for 5 h more. Followed filtration, the solids were washed with THF and DMF. The combined filtrate was concentrated to afford the product (130 mg, Yield: 82%).

Workup

  1. filtrationFollowed filtration
  2. washthe solids were washed with THF and DMF
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-8eae363e3e174363928ec9a92fcba579
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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