4-Piperidinecarbonitrile, 4-phenyl- → 1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpiperidine-4-carbonitrile

HRID 1446320Notes

Reaction equation

HRID 1446320 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]2([C:28]#[N:29])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[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:25]2[CH2:24][CH2:23][C:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]#[N:29])[CH2:27][CH2:26]2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1811384-Piperidinecarbonitrile, 4-phenyl-HCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 591701081-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}-4-phenylpiperidine-4-carbonitrile

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-phenylpiperidine-4-carbonitrile (10 mg, 0.054 mmol, 1.2 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 C23H21N3O2: 371.1634, found 371.1635.

Workup

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

Sources & evidence

ORD record
ord-c7da574f6a0e4ebf97e0f0d71ac805e5
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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