Hydrochloric Acid → HCID 67854283, compound

To a solution of (1RS,2SR)-5-methyl-1-phenyl-2-(3-piperidinopropylamino)hexan-1-ol (1.66 g, 5 mmol) in toluene (25 ml) was added sodium hydride (0.14 g, 6 mmol) and the mixture was refluxed for 1 hour. To the reaction mixture was added methyl tosylate (1.12 g, 6 mmol) and the resulting mixture was refluxed for further 1 hour. After being cooled, the mixture was washed twice with water and once with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform) to give 1.1 g of oily matter. To a solution of the matter in acetone (20 ml) was added concentrated hydrochloric acid (0.1 ml) and the mixture was concentrated under reduced pressure. The residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml) to obtain 0.45 g of the title compound as white crystals (yield: 21%).

1. temperaturethe mixture was refluxed for 1 hour
2. temperaturethe resulting mixture was refluxed for further 1 hour
3. temperatureAfter being cooled
4. washthe mixture was washed twice with water and once with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by neutral alumina column chromatography (alumina: 40 g, eluent: chloroform)
8. customto give 1.1 g of oily matter
9. concentrationthe mixture was concentrated under reduced pressure
10. customThe residue was recrystallized from acetone (10 ml)-ethanol (0.2 ml)

ORD record

ord-aabc9d85e47e46cba8039f597fdfbfe0

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250546