Potassium Hydroxide → 4-Difluoromethoxy-piperidine

4-(difluoromethoxy)piperidine-1-carbaldehyde (17) (2.7 g, 15.07 mmol) and potassium hydroxide (2.96 g, 52.74 mmol) were dissolved in water (40 mL) and stirred vigorously for 3 hours. The reaction was extracted with diethyl ether (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford an orange liquid. The crude product was purified by distillation at 0.70 mBar, collecting fractions that distilled at 25° C. to afford the desired material as a colourless oil (1.100 g, 48.3%); 1H NMR (400.132 MHz, CDCl3) δ 1.50 (1H, s), 1.66-1.57 (2H, m), 1.95-1.89 (2H, m), 2.70-2.64 (2H, m), 3.09 (2H, dt), 4.25-4.19 (1H, m), 6.24 (1H, t).

1. extractionThe reaction was extracted with diethyl ether (3×75 mL)
2. dry with materialthe organic layer was dried over MgSO4
3. filtrationfiltered
4. customevaporated
5. customto afford an orange liquid
6. distillationThe crude product was purified by distillation at 0.70 mBar
7. customcollecting fractions
8. distillationthat distilled at 25° C.

ORD-Eintrag

ord-1f0d51340769469894af7fb14d2d5fb6

Quelldatensatz

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08129380B2