Hydrochloric Acid → 4-[2-[1-(2-Hydroxyethyl)cyclohexyl]ethyl]morpholine

After adding concentrated hydrochloric acid (0.5 mL, 6.0 mmol) to a solution of 4-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]morpholine (1.31 g, ca. 1.97 mmol) in methanol (10 mL) at room temperature, the mixture was stirred for 4.5 hours. The reaction mixture was then concentrated under reduced pressure, 1N hydrochloric acid (10 mL) was added to the obtained residue, and extraction was performed with diethyl ether. After adding 5N aqueous sodium hydroxide to the aqueous layer to adjust the pH to 12, extraction was performed with diethyl ether. The organic layer was dried (anhydrous sodium sulfate) and then the solvent was distilled off under reduced pressure to obtain the title compound as a colorless oil (448 mg) (94% yield, 2 steps).

1. concentrationThe reaction mixture was then concentrated under reduced pressure, 1N hydrochloric acid (10 mL)
2. additionwas added to the obtained residue, and extraction
3. additionAfter adding 5N aqueous sodium hydroxide to the aqueous layer
4. extractionto 12, extraction
5. dry with materialThe organic layer was dried (anhydrous sodium sulfate)
6. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-b05445d2cc234bd69232bc0538b13fa0

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601843B2