2-Chloroethyldiisopropylammonium chloride → 2-[2-[[N,N-bis(1-Methylethyl)]amino]ethyl]-2H-isoindole-1,3-dione, hydrochloride

HRID 4202Notes

Reaction equation

HRID 4202 reaction equation
Cl.[CH:2]([N:5]([CH:9]([CH3:11])[CH3:10])[CH2:6][CH2:7][Cl:8])([CH3:4])[CH3:3].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[ClH:8].[CH3:3][CH:2]([N:5]([CH2:6][CH2:7][N:16]1[C:12](=[O:22])[C:13]2[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:15]1=[O:17])[CH:9]([CH3:11])[CH3:10])[CH3:4]

Participants

4

Reactant 2

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 136551592-[2-[[N,N-bis(1-Methylethyl)]amino]ethyl]-2H-isoindole-1,3-dione, hydrochlorideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-diisopropylaminoethyl chloride hydrochloride (40.0 g, 0.2 mole) and potassium phthalimide (74.0 g, 0.4 mole) as stirred overnight at 85° C. in 500 ml of dimethyl formamide. The reaction mixture was stirred to dryness on a rotary evaporator, and the residue was partitioned between chloroform and water. The chloroform layer was extracted with 10% sodium hydroxide. After drying and removal of solvent, a brown oil was obtained which slowly crystallized. A portion of the oil was converted to the hydrochloride salt and recrystallized from methanol/diethyl ether to give 4.18 g (62.3%) of white crystalline product, m.p. 209°-211° C.

Workup

  1. customthe residue was partitioned between chloroform and water
  2. extractionThe chloroform layer was extracted with 10% sodium hydroxide
  3. customAfter drying
  4. customremoval of solvent
  5. customa brown oil was obtained which
  6. customslowly crystallized
  7. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-e0ed1f7a66854e2588702449ee9bd2ce
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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