Methanol → N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride

Participants

Reaction Steps

To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol) is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% NaOH, extracted with Et2O 4×, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°-175° C.).

Provenance & Evidence