Ammonia → 2-Amino-4-(benzyloxy)-2-methylbutanonitrile

Temperature

60 °C

5.31 g (108.3 mmol) of sodium cyanide in 10 ml of water were admixed with 6.37 g (119.1 mmol) of ammonium chloride (dissolved in 15 ml of warm water) and 9 ml (216.6 mmol) of conc. ammonia in water. Subsequently, 19.3 g (108.3 mmol) of 4-(benzyloxy)butan-2-one, dissolved in 3 ml of ethanol, were added. The mixture was stirred at RT for 15 min and at 60° C. for 2 h. Another 4 g (81.6 mmol) of sodium cyanide, 4.8 g (89.7 mmol) of ammonium chloride and 6.5 ml (156.4 mmol) of conc. ammonia in water were added and the mixture was stirred at 60° C. for a further 2 h. Then the reaction solution was cooled and 300 ml each of methylene chloride and water were added thereto. After phase separation, the aqueous phase was extracted with 300 ml of methylene chloride. The combined organic phases were dried and concentrated. The crude product was purified using silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1). 19.9 g of the target compound (77% purity, 69% of theory) were obtained.

1. additionwere added
2. stirringthe mixture was stirred at 60° C. for a further 2 h
3. temperatureThen the reaction solution was cooled
4. customAfter phase separation
5. extractionthe aqueous phase was extracted with 300 ml of methylene chloride
6. customThe combined organic phases were dried
7. concentrationconcentrated
8. customThe crude product was purified

ORD record

ord-bf712c3c974646e6803ffd58272912e2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422285B2