Hydrochloric Acid → 1062625-66-4

Temperature

25 °C

Tert-butyl 4-(2-morpholinoethoxy)piperidine-1-carboxylate (78) (7.0 g, 22.26 mmol) was added to 6.0 HCl in propan-2-ol (30 mL, 180.00 mmol) and the reaction was stirred at 25° C. for 2 hours. The reaction mixture was evaporated to dryness and redissolved in methanol (75 mL) and water (7 mL), this was basified by stirring with solid sodium hydroxide for 1 hour. The reaction was filtered and evaporated to afford a gummy solid. This was stirred with ethyl acetate (75 mL) for 20 minutes, filtered and evaporated to afford a clear liquid. The crude product was purified by distillation at 1.2 mBar, collecting fractions that distilled at 120° C. to afford the desired material as a colourless oil (3.10 g, 65.0%); 1H NMR (400.132 MHz, CDCl3) δ 1.47-1.38 (2H, m), 1.93-1.89 (2H, m), 2.53-2.51 (4H, m), 2.63-2.56 (4H, m), 3.08 (2H, dt), 3.38-3.31 (1H, m), 3.61 (2H, t), 3.71 (4H, dd).

1. customThe reaction mixture was evaporated to dryness
2. dissolutionredissolved in methanol (75 mL)
3. stirringby stirring with solid sodium hydroxide for 1 hour
4. filtrationThe reaction was filtered
5. customevaporated
6. customto afford a gummy solid
7. filtrationfiltered
8. customevaporated
9. customto afford a clear liquid
10. distillationThe crude product was purified by distillation at 1.2 mBar
11. customcollecting fractions
12. distillationthat distilled at 120° C.

ORD record

ord-f415306133874765b283328728504d30

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129380B2