N-(2,3-Epoxypropyl)phthalimide → 2-[2-Hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

HRID 745523Notes

Reaction equation

HRID 745523 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[N:16]1([CH2:22][C:23]2[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)(Cl)Cl>[OH:1][CH:2]([CH2:3][O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:24]=1)[CH2:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14]

Participants

4

Reactant 2

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 8269741-(3-Hydroxybenzyl)piperidine

Product 1

HCID 134690342-[2-Hydroxy-3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

18.7 g (0.092 mole) of 2-(oxiranylmethyl)-1H-isoindole-1,3-(2H)-dione are mixed with 17.5 g (0.092 mole) of 3-(1-piperidinylmethyl)-phenol and the resulting mixture heated for 10 minutes to 130° C. After cooling, the reaction mixture is dissolved in 200 ml of chloroform and the organic phase is washed three times in succession with 30 ml of 1N NaOH-solution, then with 30 ml of water and finally with 30 ml of saturated aqueous NaCl-solution. After the organic phase has been dried over Na2SO4, it is concentrated in vacuo. The residue contains the title compound in the form of a viscous oil.

Workup

  1. temperaturethe resulting mixture heated for 10 minutes to 130° C
  2. temperatureAfter cooling
  3. washthe organic phase is washed three times in succession with 30 ml of 1N NaOH-solution
  4. dry with materialAfter the organic phase has been dried over Na2SO4, it
  5. concentrationis concentrated in vacuo

Sources & evidence

ORD record
ord-8d8a93e720aa4747826263d29dd6ab6b
Source dataset
uspto-grants-1986_07
Patent number
US04599346

Reaction notes

Loading…