Acetaldehyde → HCID 19823745, compound

Temperature

0 °C

A 1.55M solution of n-butyllithium in hexane (129 ml) was added to a stirred solution of diisopropylamine (22.3 g) in dry tetrahydrofuran (90 ml) and the resulting mixture was stirred for 30 minutes at 0° C. The mixture was then cooled to -70° C. in an acetone/dry ice bath and a solution of 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetonitrile (30 g prepared as described in Example A) in dry tetrahydrofuran (100 ml) was added to the reaction mixture under nitrogen over 50 minutes at -70° C. and then stirred for 11/2 hours at a temperature of less than 5° C. The mixture was then cooled to -70° C. and treated with a solution of acetaldehyde (13.6 g) in dry tetrahydrofuran (40 ml). After the mixture had been stirred for 1 hour at -70° C. under nitrogen the mixture was treated with excess saturated ammonium chloride solution and allowed to warm to 0° C. The aqueous layer was then separated and extracted with ether. The extract was combined with the organic phase of the reaction mixture, dried and the solvents removed by evaporation to give an oil which was distilled (eliminating hydrogen cyanide) (154°-160° C./5 mm Hg) to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminopropan-2-one.

1. temperatureThe mixture was then cooled to -70° C. in an acetone/dry ice bath
2. stirringstirred for 11/2 hours at a temperature of less than 5° C
3. temperatureThe mixture was then cooled to -70° C.
4. stirringAfter the mixture had been stirred for 1 hour at -70° C. under nitrogen the mixture
5. temperatureto warm to 0° C
6. customThe aqueous layer was then separated
7. extractionextracted with ether
8. customdried
9. customthe solvents removed by evaporation
10. customto give an oil which
11. distillationwas distilled (eliminating hydrogen cyanide) (154°-160° C./5 mm Hg)

ORD record

ord-9b5b37e4572f4a11844bf09db13aca9a

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05047432