Hydrochloric Acid → HCID 68577617, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence