1-Benzyl-3-hydroxypiperidine

Colorless liquid

N-BENZYL-3-PIPERIDONE HYDROCHLORIDE was converted to the free base by addition to aqueous K2CO3 followed by extraction into ethyl acetate. To a solution of N-benzyl-3-piperidone (2.19 g, 11.57 mmol) in ethanol was added sodium borohydride (NaBH4) (0.438 g, 11.57 mmol) slowly over ten minutes. The solution was allowed to stir at room temperature overnight, and then concentrated in vacuo. The residue was dissolved in 1.0 N HCI and washed twice with diethylether, then the aqueous solution was basified with 3.0 N KOH to a pH of 12, and then extracted 3 times with dichloromethane. The organic extract was then dried over NA2SO4, and concentrated in vacuo. The crude was determined to be 100percent pure (1.900 g, 86percent) by IC/MS (EI) : m/z 192.3 (M + 1)Ethanol (1 L) and 1-benzyl-3-hydroxypyridinium chloride (50 g) were added to the reaction flask. Sodium borohydride (43 g) was added in portions at a temperature not exceeding 25 ° C, and after heating, it was heated to reflux. The reaction is carried out for 2~3 hours, the reaction is complete, cooled to 0~10 °C, hydrochloric acid is added dropwise, and the pH is adjusted to 8, The solvent was concentrated under reduced pressure, and ethyl acetate and saturated brine were added and dissolved. The product in the aqueous phase was extracted twice with ethyl acetate. The ethyl acetate phase was combined, dried over anhydrous sodium sulfate and filtered. Concentrated to dryness to give a pale yellow oil, 38.9 g.REFERENCE EXAMPLE 4 Methanol (10 L) and 1-benzyl-3-hydroxypyridinium bromide (500 g) were added to the reaction flask. Sodium borohydride (215 g) was added in portions at a temperature not exceeding 25 ° C. After the addition was completed, it was heated to reflux. After reacting for 4 hours, the reaction was completed, and the mixture was cooled to 0 to 10 ° C. Hydrochloric acid was added dropwise, and the pH was adjusted to 8. The solvent was concentrated under reduced pressure, dissolved in ethyl acetate and saturated brine, and the mixture was separated. In the product twice, The combined ethyl acetate phases were dried over anhydrous sodium sulfate and filtered. Concentrated to dryness afforded 342.6 g of pale yellow oil.

Molecular Weight:191.27
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:191.131014166
Monoisotopic Mass:191.131014166
Topological Polar Surface Area:23.5
Heavy Atom Count:14
Complexity:166
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes