Hydrochloric Acid → HCID 68548579, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (1RS,2SR)-3-(methylamino)-1-[methyl(4-methylphenyl)amino]-1-phenylpropan-2-ol hydrochloride (Example 12, 83 mg, 0.23 mmol) in formic acid (0.4 mL) at 50° C., was added an aqueous solution of formaldehyde (37% in water, 0.16 mL). The reaction was heated at 70° C. for 1 hour, then poured into water (10 mL) and basified to pH 10 with the addition of an aqueous solution of sodium hydroxide (2 N). The product was extracted with ethyl acetate (3×10 mL), and the combined organic extracts were dried (anhydrous sodium sulfate) and concentrated to yield 59 mg (86%) 1RS,2SR)-3-(dimethylamino)-1-[methyl(4-methylphenyl)amino]-1-phenylpropan-2-ol as a viscous, colorless liquid. The product was dissolved in ethanol (0.5 mL) and treated with a solution of hydrochloric acid (0.1 mL, 4 M in 1,4-dioxane). All volatiles were again removed under reduced pressure. The resulting white solid was recrystallized (isopropanol/ethyl ether/−20° C.) to yield 64 mg (75%) of (1RS,2SR)-3-(dimethylamino)-1-[methyl(4-methylphenyl)amino]-1-phenylpropan-2-ol hydrochloride as a white powder. MS (ESI) m/z 299.1 ([M−H]+); HRMS: calculated for C19H26N2O+H, 299.2118; found (ESI, [M+H]+), 299.2109.

Provenance & Evidence