2-Chloro-N,N-dimethylethylamine → HCID 17851263, compound

HRID 497827Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:27])[N:10]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:13]=1.[CH3:28][N:29]([CH2:31][CH2:32]Cl)[CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:27])[N:10]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:32][CH2:31][N:29]([CH3:30])[CH3:28])=[CH:24][CH:25]=2)[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(2-Chlorophenyl)-5-(2-pyridyl)-1-(4-hydroxyphenyl)-1,2-dihydropyridin-2-one (82 mg) and 57 mg of N,N-dimethylaminoethyl chloride were dissolved in 2 ml of dimethylformamide, 55 mg of potassium carbonate were added thereto at 60° C. and the mixture was stirred for one night. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated in vacuo and purified by an NH silica gel column chromatography (hexane-ethyl acetate system) to give 27 mg of the title compound.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with a saturated saline solution
dry with materialdried over anhydrous magnesium sulfate
filtrationThe drying agent was filtered off
concentrationthe filtrate was concentrated in vacuo
custompurified by an NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record: ord-b990f2b4504e4199b6f2a49dd9abd8ba
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949571B2

Reaction notes

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