Acetonitrile → 4-(4-Methoxyphenyl)-1-(4-phenylbutyl)piperidine

HRID 1955226Notes

Reaction equation

HRID 1955226 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][C:23]#N>>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:8][CH2:7][CH2:10][CH2:11][C:22]3[CH:23]=[CH:6][CH:5]=[CH:4][CH:9]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 222528534-(4-Methoxyphenyl)piperidine hydrochloride

Product 1

HCID 98836884-(4-Methoxyphenyl)-1-(4-phenylbutyl)piperidine

Procedure

The title compound was prepared from 4-(4-methoxyphenyl)piperidine hydrochloride (1.00 g, 4.39 mmol), 4-phenyl-p-tosylbutane (1.40 g, 4.61 mmol) and K2CO3 (1.24 g, 9.00 mmol) in CH3CN (25 mL) as a beige solid (979 mg, 69%): mp 48-50° C.; 1H NMR (CDCl3) 1.52-1.86 (m, 8H), 2.01 (td, J=11 and 3.6 Hz, 2H), 2.34-2.50 (m, 3H), 2.65 (t, J=7.2 Hz, 2H), 2.98-3.08 ((m, 2H), 3.79 (J, 3H), 6.85 (d, J=8.7 Hz, 2H), 7.12-7.32 (m, 7H).

Sources & evidence

ORD record
ord-6869da8ad60d48319c55cebedcd6873c
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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