(+-)-Anabasine → 3-(1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-2-yl)pyridine

HRID 1446323Notes

Reaction equation

HRID 1446323 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.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=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:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2181(+-)-AnabasineHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 591701333-(1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-2-yl)pyridine

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 3-piperidin-2-ylpyridine (11 mg, 0.045 mmol, 1.0 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 C21H21N3O2: 347.1634, found 347.1644.

Workup

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

Sources & evidence

ORD record
ord-e6a63e09aef54585ac80f15a38be74c4
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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