4-Benzyl-4-piperidinol → 4-Benzyl-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}piperidin-4-ol

HRID 1446331Notes

Reaction equation

HRID 1446331 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.[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][N:26]([C:13]([C:9]2[CH:10]=[N:11][O:12][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[O:14])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 981524-Benzyl-4-piperidinolHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 591700364-Benzyl-1-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}piperidin-4-ol

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 4-benzylpiperidin-4-ol (9.5 mg, 0.050 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 C23H24N2O3: 376.1787, found 376.1790.

Workup

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

Sources & evidence

ORD record
ord-ce5caf20609745ffb701b858435bfa4b
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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