Hydrazine hydrate (1:1) → 1-Amino-3-{3-[(piperidin-1-yl)methyl]phenoxy}propan-2-ol

Participants

Reaction Steps

A solution of 7.7 g (0.019 mole) of 2-[2-hydroxy-3-[3-(1-piperidinylmethyl)-phenoxy]-propyl]-1H-isoindole-1,3-(2H)-dione and 2.9 ml of hydrazine hydrate (80% aqueous solution) in 80 ml of ethanol is heated for 3 h to reflux temperature. After the reaction solution has cooled, the solid formed is separated off, the solution is concentrated in vacuo and the residue is dissolved in 80 ml of water. 7.2 ml of conc. HCl are added to the aqueous solution which is then filtered off under suction from the solid precipitated, after which the aqueous solution is adjusted to pH 12 with 2N NaOH and repeatedly extracted with acetic acid ethyl ester. The organic solvent is concentrated in vacuo and the residue purified by distillation (B.p.0.008 =140°-160° C.). After the addition of petroleum ether to the distillate, the title compound crystallizes out.

Provenance & Evidence