1-(3-Benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine → 1-(3-Hydroxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine

HRID 1741396Notes

Reaction equation

HRID 1741396 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]1[O:21][C:22]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1)=[O:13])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]1[O:21][C:22]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1)=[O:13]

Participants

4

Reactant 1

HCID 183673361-(3-Benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine

Product 1

HCID 183673151-(3-Hydroxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidineYield 127.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3-benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine (95 mg) and 10% Pd-C (50% wet, 15 mg) in ethyl acetate (3 ml) -10% methanolic hydrogen chloride was stirred in the cresence of atmospheric H2 gas at room temperature for 7 hours and filtered. The filtrate was evaporated in vacuo to afford 1-(3-hydroxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine (100 mg) as a crude oil.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-32b557acec704d689483d5a6d859dad3
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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