4-Benzyl-2-(chloromethyl)morpholine → 2-((4-benzylmorpholin-2-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1608205Notes

Reaction equation

HRID 1608205 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14]Cl)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:21]2[C:20](=[O:22])[C:19]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]3[C:17]2=[O:27])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 28015624-Benzyl-2-(chloromethyl)morpholineHCID 24194345Phthalimide potassium salt

Product 1

HCID 117245602-((4-benzylmorpholin-2-yl)methyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-benzyl-2-chloromethylmorpholine (86.4 g), phthalimide potassium salt (78.0 g), and dimethylformamide (700 ml) is refluxed with stirring for 5 hours. The reaction mixture is poured into ice-water. The resulting precipitate is collected and recrystallized from isopropyl alcohol to give N-[(4-benzyl-2-morpholinyl)methyl]phthalimide (107 g), mp 136°-139° C. The starting material, 4-benzyl-2-chloromethylmorpholine, is prepared according to the method of F. Loftus [Syn. Commun., 10, 59-73 (1980)].

Workup

  1. temperatureis refluxed
  2. customThe resulting precipitate is collected
  3. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-a95fe3e6743a483a90fc136479b8b659
Source dataset
uspto-grants-1989_09
Patent number
US04870074

Reaction notes

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