Water → 2-[3-[4-[2-(Dimethylamino)ethyl]phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

HRID 325685

Reaction equation

HRID 325685 reaction equation
[CH3:1][N:2]([CH3:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29].O>CN(C)C=O>[CH3:12][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH2:17][CH2:18][N:19]2[C:23](=[O:24])[C:22]3[C:21](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:20]2=[O:29])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 68313Hordenine

Product 1

HCID 212975672-[3-[4-[2-(Dimethylamino)ethyl]phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[2-(dimethylamino)ethyl]phenol (4.13 g) and sodium hydride (0.67 g) in dimethylformamide was stirred at room temperature for 24 h. N-(3-Bromopropyl) phthalimide (6.7 g) was added at 0° and stirring was continued for 24 h. The solution was treated with water and extracted with ether. Evaporation of the solvent gave the title compound as a white solid which was recrystallised from light petroleum (b.p. 60°-80°) 2.3 g) m.p. 81°-82°. TLC silica; ethyl acetate:water:isopropanol:0.88 ammonia 25:8:15:2; Rf 0.45.

Workup

  1. stirringstirring
  2. waitwas continued for 24 h
  3. extractionextracted with ether
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-573cd8af303547738e106d07828ba5ad
Source dataset
uspto-grants-1984_04
Patent number
US04442110

Linked notes

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