Methyl chloroformate → HCID 61056118, compound

Temperature

0 °C

(1-Methyl-4-methylamino-piperidin-4-yl)-methanol is prepared from 4-amino-piperidine-4-carboxylic acid 2HCl. Methyl chloroformate (0.40 g, 4.2 mmol) is added dropwise to a mixture of 4-amino-piperidine-4-carboxylic acid 2HCl (0.278 g, 1.28 mmol) and Et3N (0.713 g, 7.04 mmol) in THF (10 ml) at room temperature. After 16 h, the reaction mixture is filtered, rinsed with EtOAc and concentrated. A solution of LAH in THF (5 ml of a 1 M solution) is added to the residue. After stirring at reflux for 4 h, the reaction mixture is cooled to 0° C. and carefully quenched with Na2SO4.10H2O. After warming to room temperature the reaction mixture is diluted with EtOAc and filtered through Celite. The filtrate is concentrated to give (1-methyl-4-methylamino-piperidin-4-yl)-methanol which is carried forward without purification.

1. filtrationthe reaction mixture is filtered
2. washrinsed with EtOAc
3. concentrationconcentrated
4. additionA solution of LAH in THF (5 ml of a 1 M solution) is added to the residue
5. temperatureat reflux for 4 h
6. customcarefully quenched with Na2SO4.10H2O
7. temperatureAfter warming to room temperature the reaction mixture
8. additionis diluted with EtOAc
9. filtrationfiltered through Celite
10. concentrationThe filtrate is concentrated

ORD record

ord-8d343d87b52b41f5af8d26513d152a07

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585975B2