Potassium Cyanide → 4-Aminooxane-4-carbonitrile

Temperature

70 °C

To a solution of tetrahydropyran-4-one (150 g, 1.50 mol) in methanol (1500 mL) was added potassium cyanide (6.0 M in water, 400 mL, 2.4 mol), ammonium hydroxide (25% solution in water, 1000 mL, 7.4 mol), and ammonium chloride (161 g, 3.00 mol). The reaction mixture was heated to 70° C. After 16 hours, the reaction mixture was cooled, quenched with cold brine (2000 mL), and extracted with dichloromethane (4×1500 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 4-amino-tetrahydro-2H-pyran-4-carbonitrile. The material was used without further purification.

1. temperaturethe reaction mixture was cooled
2. customquenched with cold brine (2000 mL)
3. extractionextracted with dichloromethane (4×1500 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-bc1690f80d844892ad921697e3c8cd9d

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987456B2