Hydrochloric Acid → HCID 13671866, compound

Temperature

110 °C

A mixture of 2-bromo-5-methyl-1-phenylhexan-1-ol [prepared from 2-bromo-5-methyl-1-phenylhexan-1-one by usual NaBH4 -reduction] (1.0 g, 3.69 mmol) and 1-(3-aminopropyl)piperidine (1.05 g, 7.38 mmol) was heated at 110° C. for 4 hours in a nitrogen atmosphere. After being cooled, the reaction mixture was dissolved in lN-HCl (50 ml) and the solution was washed with ether. The aqueous layer was basified with lN-NaOH and then extracted twice with ether. The combined ethereal extract was washed three times with water, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by preparative TLC to give pale yellow oily matter. To a solution of the matter in ethanol was added in excess 18% HCl in EtOH and the resulting mixture was evaporated under reduced pressure. The residue was dissolved with heating in ethanol (15 ml) and to the mixture was then added 10 ml of acetone. The mixture was stirred at room temperature. Precipitated crystals were collected by filtration to obtain 0.52 g of the title compound (yield: 35%).

1. temperatureAfter being cooled
2. washthe solution was washed with ether
3. extractionextracted twice with ether
4. extractionThe combined ethereal extract
5. washwas washed three times with water
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by preparative TLC
9. customto give pale yellow oily matter
10. customthe resulting mixture was evaporated under reduced pressure
11. dissolutionThe residue was dissolved
12. temperaturewith heating in ethanol (15 ml) and to the mixture
13. additionwas then added 10 ml of acetone
14. customPrecipitated crystals
15. filtrationwere collected by filtration

ORD record

ord-7f85dc92a3c942ee86330729871835d4

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05250546