Hydroxyamine hydrochloride → 1-Benzyl-4-piperidylamine

To a solution of hydroxylamine hydrochloride (3.67 g, 52.8 mmol) in water (10 mL) and ethyl alcohol (80 mL) was added 1-benzyl piperidone (10.0 g, 52.8 mmol) at room temperature. The reaction mixture was heated to reflux for 4 h and then stirred at room temperature overnight. The resulting white solid was filtered, washed with ether and dried (8.4 g, 80%). It was added in small portions to a suspension of lithium aluminum hydride (2.3 g, 60.0 mmol) in diethyl ether (150 mL) at room temperature and the suspension was heated to reflux for 8 h. The reaction mixture was cooled to 0° C. and quenched with successive addition of water (3 mL), 3 N NaOH (3 mL) and water (9 mL). The white suspension was filtered and the filtrate was dried over MgSO4. The solvent was removed in vacuo after filtration. 4-Amino-1-benzyl-piperidine was obtained as a colorless oil (6.0 g). It was used in the next step without purification.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 4 h
3. filtrationThe resulting white solid was filtered
4. washwashed with ether
5. customdried (8.4 g, 80%)
6. temperaturethe suspension was heated
7. temperatureto reflux for 8 h
8. temperatureThe reaction mixture was cooled to 0° C.
9. customquenched with successive addition of water (3 mL), 3 N NaOH (3 mL) and water (9 mL)
10. filtrationThe white suspension was filtered
11. dry with materialthe filtrate was dried over MgSO4
12. customThe solvent was removed in vacuo
13. filtrationafter filtration

ORD record

ord-7de63dc7616e4dec97aa5739b2a768a1

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06245773B1