N-[4-(benzyloxy)phenyl]-4-(2-tert-butylphenyl)piperazine-1-carboxamide → 4-(2-tert-butylphenyl)-N-(4-hydroxyphenyl)piperazine-1-carboxamide

HRID 534966Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:20][CH2:19]2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[N:21]1[CH2:20][CH2:19][N:18]([C:16]([NH:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)=[O:17])[CH2:23][CH2:22]1)([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of N-[4-(benzyloxy)phenyl]-4-(2-tert-butylphenyl)piperazine-1-carboxamide (Example 173, 2.0 g, 4.51 mmol) and palladium hydroxide (20% on carbon, wetted with ca. 50% water, 100 mg) in ethyl acetate (100 mL) was stirred under hydrogen at 60° C. for 16 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 30:70) to provide 4-(2-tert-butylphenyl)-N-(4-hydroxyphenyl)piperazine-1-carboxamide (1.47 g, 92%) as a white solid.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 30:70)

Sources & evidence

ORD record: ord-24147237abf6434580a3e350e9460c35
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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