Methyl vinyl ketone → 4-(4-Chlorobenzyl)-1-(3-hydroxybutyl)piperidine hydrochloride

HRID 1861789

Reaction equation

[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH:15]([C:17]([CH3:19])=[O:18])=[CH2:16]>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:16][CH2:15][CH:17]([OH:18])[CH3:19])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-(4-chlorobenzyl)piperidine (1.0 g, 4.78 mmol) in methyl vinyl ketone (1.0 ml) was added H2O (1 drop) and the resulting solution stirred at 110° C. for 2 h. The crude mixture was purified by filtration on silica gel using CH2Cl2/MeOH as eluant to afford the title compound (1.20 g, 90%) as a pale yellow oil: 1H NMR (CDCl3) 1.35-1.55 (m, 5H), 1.63 (d, J =12.3, 2H), 2.055 (t, J=9.6, 2H), 2.154 (s, 2H), 2.40 (d, J=6.3, 2H), 2.748 (s, 2H), 2.972 (d, J=11.4, 2H), 7.034 (d, J=8.1, 2H), 7.218 (d, J=8.1, 2H).

Workup

filtrationThe crude mixture was purified by filtration on silica gel

Sources & evidence

ORD record: ord-b6dc239fda38498186408720a1816c34
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06534522B2

Linked notes

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