Isopropanol → 1-Benzyl-4-(ethylamino)piperidine-4-carbonitrile

To a solution of 1-benzylpiperidin-4-one (5.69 g) in ethanol (4.2 mL) was added dropwise a solution of ethylamine hydrochloride (2.69 g) in water (3 mL) under ice-cooling and then added dropwise a solution of potassium cyanide (2.04 g) in water (7 mL) and the mixture was stirred at room temperature overnight. To the reaction mixture was added isopropyl alcohol (10 mL) and water (30 mL) and the mixture was stirred and extracted. To the organic layer was added water (30 mL) and the mixture was stirred and extracted. The organic layer was diluted with methylene chloride (30 mL) and the mixture was washed with a brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and to the residue was added isopropyl alcohol (100 mL) and the precipitates were filtered off. The filtrate was concentrated in vacuo to give 1-benzyl-4-cyano-4-(ethylamino)piperidine (7.3 g, yield: 99.7%) as a yellow oil.

1. temperaturecooling
2. stirringthe mixture was stirred
3. extractionextracted
4. additionTo the organic layer was added water (30 mL)
5. stirringthe mixture was stirred
6. extractionextracted
7. additionThe organic layer was diluted with methylene chloride (30 mL)
8. washthe mixture was washed with a brine
9. dry with materialdried over magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated in vacuo and to the residue
12. additionwas added isopropyl alcohol (100 mL)
13. filtrationthe precipitates were filtered off
14. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-17923bd4236441f19f29a3289906e677

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872006B2