Azacyclonol → (1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-4-yl)(diphenyl)methanol

HRID 1446332Notes

Reaction equation

HRID 1446332 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[C:16]1([C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[OH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:27]2[CH2:26][CH2:25][CH:24]([C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[OH:23])[CH2:29][CH2:28]2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 15723AzacyclonolHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 59170032(1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-4-yl)(diphenyl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (10 mg, 0.045 mmol) in dichloromethane (1 mL) was added diphenyl(piperidin-4-yl)methanol (13.3 mg, 0.074 mmol, 1.1 eq.), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C29H28N2O3: 452.2100, found 452.2107.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-046351f23d0d497a9fb0876c92aa773a
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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