Potassium Cyanide → 4-(3-Hydroxypiperidino)-tetrahydro-4h-thiopyran-4-carbonitrile

Reaktionsgleichung

Cl.[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[C-:9]#[N:10].[K+].[S:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1>O>[OH:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:15]2([C:9]#[N:10])[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[CH2:4]1

Komponenten

Versuchsvorschrift

3-hydroxy-piperidine hydrochloride (6.5 g, 47.3 mmoles) in 30 ml of water is introduced into a 100 ml two-necked flask. Potassium cyanide (1.85 g, 35.5 mmoles) is added and tetrahydro-4H-thiopyran-4-one (2.7 g, 23.6 mmoles) is introduced dropwise. The pH of the medium is adjusted to 11 with a few drops of soda (10%). After 24 hours under agitation at ambient temperature, extraction with ether (3×80 ml) is carried out, the combined organic phases are washed with water (100 ml), dried over Na2SO4, filtered and concentrated to dryness. In this way, a colourless oil is obtained (3.9 g, 17.2 mmoles).