Potassium Cyanide → 4-Aminothiane-4-carbonitrile

To a solution of tetrahydro-4H-thiopyran-4-one (500 mg) in water/ethanol (10 mL/10 mL) was added potassium cyanide (1.4 g) and ammonium chloride (1.15 g) and the mixture was stirred at room temperature for 4 days. To the reaction mixture was added diethylether and an aqueous 1N sodium hydroxide solution and the mixture was stirred. The organic layer was separated and the aqueous layer was extracted with diethylether and ethyl acetate. The combined organic layer was dried over calcium chloride and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=70/30 to 30/70) to give 4-amino-4-cyano-tetrahydro-4H-thiopyrane (315 mg) as a colorless solid.

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted with diethylether and ethyl acetate
3. dry with materialThe combined organic layer was dried over calcium chloride
4. filtrationfiltered
5. concentrationThe filtrate was concentrated in vacuo
6. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=70/30 to 30/70)

ORD record

ord-f46206e0c55345a7a5c70751d4b04643

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188097B2