Water → 4-Phenylpiperidine-4-methanol

A solution of 4-phenyl-piperidine-4-carboxylic acid (0.168 g, 0.819 mmol) in THF (2 mL) was added dropwise to a 0° C. solution of lithium aluminum hydride (1.0N in THF, 1.63 mL, 1.64 mmol). The reaction was stirred at room temperature for about 16 h. Water (1 mL) was added to the reaction mixture, followed by 2 N NaOH (1 mL). The solution was stirred for about 1 h then filtered. The filtrate was extracted with DCM (25 mL) and the organic layer was separated. The aqueous layer was further extracted with dichloromethane (2×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give (4-phenyl-piperidin-4-yl)-methanol (0.078 g, 0.41 mmol) as brown oil, which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method b) Rt 1.24 min; m/z: (M+H)+ 192.

1. stirringThe solution was stirred for about 1 h
2. filtrationthen filtered
3. extractionThe filtrate was extracted with DCM (25 mL)
4. customthe organic layer was separated
5. extractionThe aqueous layer was further extracted with dichloromethane (2×25 mL)
6. dry with materialThe combined organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD-Eintrag

ord-ce1d76a895844dfb981052d595b55813

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08754107B2