2-Pyridinecarboxaldehyde → HCID 53657319, compound

(3R)-3-Piperidinol hydrochloride (10.0 g) and triethylamine (10.13 ml) in dry 1,2-dichloroethane (350 ml) were stirred for 15 minutes at 50° C. 2-Pyridine carboxaldehyde (7.63 ml) and glacial acetic acid (4.16 ml) were added and the reaction mixture stirred for 1.5 hours at reflux. Sodium triacetoxyborohydride (34.65 g) was then added portionwise and the resulting mixture was cooled to room temperature and stirred for a further 1 hour. Water (350 ml) and 1M aqueous sodium hydroxide solution were then added until the mixture was pH12. The organic layer was separated and the aqueous extracted with chloroform, the combined organic layers were dried over magnesium sulphate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent system of 95:5, by volume, chloroform:methanol to afford (3R)-1-(2-pyridinylmethyl)-3-piperidinol (8.10 g) as a brown oil.

1. temperatureat reflux
2. stirringstirred for a further 1 hour
3. customThe organic layer was separated
4. extractionthe aqueous extracted with chloroform
5. dry with materialthe combined organic layers were dried over magnesium sulphate
6. customthe solvent was removed under reduced pressure
7. customThe crude product was purified by column chromatography on silica gel eluting with a solvent system of 95:5, by volume, chloroform

ORD record

ord-03e114b68da4454982a09a32c3386ace

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06562964B1