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

HRID 1589538Notes

Reaction equation

HRID 1589538 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].[CH3:16][N:17]([CH2:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)[CH3:18].[H-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:18][N:17]([CH2:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:3][CH:2]([OH: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])[CH3:16]

Participants

6

Reactant 3

HCID 21601N-(2,3-Epoxypropyl)phthalimideHCID 24758Sodium hydrideHCID 328963-(Dimethylaminomethyl)phenol

Product 1

HCID 202460012-[3-[3-(Dimethylaminomethyl)phenoxy]-2-hydroxy-propyl]-1H-isoindole-1,3-(2H)-dioneYield 39.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(oxiranylmethyl)-1H-isoindole-1,3-(2H)-dione (20.3 g) and 3-(dimethylaminomethyl)phenol (22.3 g) in dimethylformamide (200 ml) with a catalytic amount of sodium hydride (0.2 g) was heated for 6 h at 100° under N2. The solvent was evaporated to give an oil which was dissolved in chloroform and washed with 2N sodium hydroxide and water. The organic solution was evaporated to give an oil (14 g). A portion of the oil (0.8 g) was distilled to give the title compound (0.6 g) as an oil, b.p. 250° (0.08 mmHg).

Workup

  1. customThe solvent was evaporated
  2. customto give an oil which
  3. washwashed with 2N sodium hydroxide and water
  4. customThe organic solution was evaporated

Sources & evidence

ORD record
ord-b92ba891a9cb4d749161f7465c9c11dd
Source dataset
uspto-grants-1986_02
Patent number
US04571394

Reaction notes

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