Ammonia → HCID 66852357, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of β-alanine (433 mg) in methanol (30 ml), sodium hydroxide (204 mg) was added. Then, trimethoxymethane (532 μl) was added to the mixture at 0° C. Further, a solution of (2E)-3-[4-(3-phenylpropoxy)phenyl]but-2-enal (1.43 g) in a mixture of methanol (30 ml) and tetrahydrofuran (10 ml) was added. The reaction mixture was stirred at 0° C. for 30 minutes. To the mixture, sodium borohydride (221 mg) was added at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. After adding 2 N hydrochloric acid (5.5 ml), the reaction mixture was concentrated. To the residue thus obtained, a mixed solvent of chloroform:methanol:aqueous ammonia=80:10:1 was added, followed by filtration. To the precipitate thus obtained, water was added and the mixture was centrifuged to give a precipitate. The obtained residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=80:20:4). To a suspension of the purified product in dioxane (100 ml) and water (15 ml), a 4 mol/l hydrogen chloride-dioxane solution (0.9 ml) was added at 0° C. The reaction mixture was concentrated and the residue was washed with diethyl ether and dried to give the title compound (1.16 g) having the following physical properties.

Provenance & Evidence