4-(2-Chlorobenzyl)-2-chloromethyl-6-methylmorpholine → N-[[4-(2-chlorobenzyl)-6-methyl-2-morpholinyl]methyl]phthalimide

HRID 1608226Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[CH2:10][CH:9]([CH3:11])[O:8][CH:7]([CH2:12]Cl)[CH2:6]1.[K].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][N:5]1[CH2:10][CH:9]([CH3:11])[O:8][CH:7]([CH2:12][N:23]2[C:22](=[O:24])[C:21]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]3[C:19]2=[O:29])[CH2:6]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(2-chlorobenzyl)-2-chloromethyl-6-methylmorpholine (19.7 g), phthalimide potassium salt (14.6 g), and dimethylformamide (150 ml) is stirred at 150° C. for 5 hours. The reaction mixture is poured into ice-water and extracted with diethyl ether. The organic layer is washed successively with water and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent is distilled off to give the title compound (26 g) as an oil.

Workup

extractionextracted with diethyl ether
washThe organic layer is washed successively with water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
distillationThe solvent is distilled off

Sources & evidence

ORD record: ord-b4daf0cac8694cad8489942fe69d50af
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04870074

Reaction notes

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