Chlorosuccinimide → 4-chloro-2,N-dimethyl-5-morpholin-4-ylbenzamide

HRID 1098315Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Cl:18]N1C(=O)CCC1=O>CN(C)C=O>[Cl:18][C:10]1[C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:8][C:3]([C:4]([NH:6][CH3:7])=[O:5])=[C:2]([CH3:1])[CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

100 mg (0.427 mmol) of 2,N-dimethyl-5-morpholin-4-ylbenzamide prepared in Step A was dissolved in 3 ml of N,N-dimethylformamide, and thereafter, 63 mg (0.47 mmol) of N-chlorosuccinimide was added thereto under cooling on ice. The obtained mixture was stirred at 50° C. for 1 hour. Thereafter, the reaction solution was concentrated, and water was then added thereto. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. The extract was concentrated, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate:methylene chloride=1:5), so as to obtain 54.5 mg (47%) of 4-chloro-2,N-dimethyl-5-morpholin-4-ylbenzamide in the form of a colorless solid, as well as 46 mg (40%) of 2-chloro-6,N-dimethyl-3-morpholin-4-ylbenzamide in the form of a colorless solid.

Workup

temperatureunder cooling on ice
concentrationThereafter, the reaction solution was concentrated
additionwater was then added
extractionThe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
concentrationThe extract was concentrated
customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate:methylene chloride=1:5)

Sources & evidence

ORD record: ord-b97a92208f8d4307a7900e85a7f3f48b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143274B2

Reaction notes

Loading…