Acetone Cyanohydrin → 4-(3-methyl-piperidino)-tetrahydro-4H-thiopyran-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Magnesium sulphate (9.6 g, 80 mmoles), DMA (2 g, 23 mmoles), (±)-3-methylpiperidine (4 g, 40 mmoles), tetrahydro-4H-thiopyran-4-one (2.3 g, 20 mmoles) and acetone cyanohydrin (1.7 g, 20 mmoles) are introduced in succession into a 250 ml two-necked flask. The reaction medium is agitated for 48 hours at 45° C. After cooling down to ambient temperature, the pasty mixture obtained is placed on ice (approximately 150) and agitated for 30 minutes. Extraction with ether is then carried out (3×80 ml), the combined organic phases are washed with water (100 ml), followed by drying over Na2SO4, filtering and concentration to dryness. A brown oil is thus obtained (4.5 g, 20 mmoles) constituted by a mixture of expected product with approximately 4% of amino nitrite originating from acetone and 7% of the remaining tetrahydro-4H-thiopyran-4-one. The product is then used without further purification.

Provenance & Evidence