Potassium Carbonate → 4-Benzyl-1-(3-butynyl)-4-hydroxypiperidine

Reaktionsgleichung

S([CH2:5][CH2:6][C:7]#[CH:8])(C)(=O)=O.[CH2:9]([C:16]1([OH:22])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:9]([C:16]1([OH:22])[CH2:21][CH2:20][N:19]([CH2:8][CH2:7][C:6]#[CH:5])[CH2:18][CH2:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

Versuchsvorschrift

A mixture of 1-mesylbut-3-yne (1.63 g, 11.0 mmol), 4-benzyl-4-hydroxypiperidine (1.91 g, 10.0 mmol) and K2CO3 (4.14 g, 30.0 mmol) in 50 mL of CH3CN is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×30 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as a colorless solid (2.1 g, 86%): mp 51-53° C.; 1H NMR (CDCl3) 1.50 (m, 2 H), 1.65 (m, 3 H), 1.97 (s, 1 H), 2.35 (m, 4 H), 2.62 (m, 4 H), 2.75 (s, 1 H), 7.21-7.31 (m, 5 H).