Hydrochloric Acid → HCID 68577617, compound

Temperature

-20 °C

To (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(methyl)amino]-1-ethanol (1.47 g, 9.1 mmol) produced in Example 10, toluene (10.02 g) and triethylamine (1.70 g, 3.5 equivalents) were added. The mixture was cooled to −20° C. Methanesulfonyl chloride (1.76 g, 3.2 equivalents) was added dropwise thereto, and then allylamine (1.71 g, 6.0 equivalents) was added dropwise thereto. The mixture was stirred for 1 hour. The temperature of the mixture was raised to 25° C., and then the mixture was stirred for 12 hours. To the mixture, 10 wt % aqueous solution of sodium carbonate (10.02 g) was added. After the organic layer and aqueous layer were separated, the organic layer was washed twice with distilled water (10 mL). The obtained organic layer was concentrated. To the concentrate, 28 wt % hydrogen chloride solution in isopropanol (1.42 g, 2.2 equivalents) and acetone (20 mL) were added to precipitate crystals. The mixture was stirred at 25° C. for 1 hour, then the crystals were separated by filtration under reduced pressure, washed with acetone (5 mL) and dried under vacuum, to obtain 1.05 g of the title compound as pale brown crystals (yield: 60%, chemical purity: 91.7 area %). The retention time in the chemical purity analysis method was 18.5 min.

1. temperatureThe temperature of the mixture was raised to 25° C.
2. stirringthe mixture was stirred for 12 hours
3. customAfter the organic layer and aqueous layer were separated
4. washthe organic layer was washed twice with distilled water (10 mL)
5. concentrationThe obtained organic layer was concentrated
6. customto precipitate crystals
7. stirringThe mixture was stirred at 25° C. for 1 hour
8. customthe crystals were separated by filtration under reduced pressure
9. washwashed with acetone (5 mL)
10. customdried under vacuum

ORD record

ord-bc55f81f87234945845bf285309d2073

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273883B2