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

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.

1. temperatureto reflux temperature
2. temperatureAfter the reaction solution has cooled
3. customthe solid formed
4. customis separated off
5. concentrationthe solution is concentrated in vacuo
6. dissolutionthe residue is dissolved in 80 ml of water
7. addition7.2 ml of conc. HCl are added to the aqueous solution which
8. filtrationis then filtered off under suction from the solid
9. customprecipitated
10. extractionrepeatedly extracted with acetic acid ethyl ester
11. concentrationThe organic solvent is concentrated in vacuo
12. distillationthe residue purified by distillation (B.p.0.008 =140°-160° C.)
13. additionAfter the addition of petroleum ether to the distillate
14. customthe title compound crystallizes out

ORD record

ord-f56c452e4d2148219e8f8d2e2f3598d7

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599346