Sodium Hydroxide → HCID 23507360, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium borohydride (63 mg, 1.68 mmol) in ethanol (1 ml) was added drop-wise to a stirred solution of 4-(4-phenylpiperazine-1-yl methyl)-nitro-aniline (1 g, 3.36 mmol) and tin (II) dichloride dihydrate (2.27 g, 10.10 mmol) in ethanol (20 ml) at 60° C. The resulting solution was stirred for 2 h after which the reaction was cooled to 0° C. and basified (pH>10) by the addition of sodium hydroxide (2M). The aqueous layer was extracted with dichloromethane (3×20 ml) and the combined organics washed with brine, then dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (hexanes/ethyl acetate 1:1) to afford the title compound as a pale yellow solid (441 mg, 49%). HPLC retention time 5.82 min. Mass spectrum (ES+) m/z 268 (M+H).

Provenance & Evidence