Dimethylamine → HCID 21194266, compound

HRID 1067838Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1.34 g (3.53 mmol) of ethyl 4-chloro-6-[4-(chloromethyl)phenoxy]-1-methyl-2-indolecarboxylate, 8.0 g of dimethylamine and 80 ml of dimethylformamide was stirred at 0° C. for 3 hours. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with saturated sodium chloride aqueous solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.29 g (21.2%) of ethyl 4-chloro-6-[4-(dimethylaminomethyl)phenoxy]-1-methyl-2-indolecarboxylate.

Workup

additionThe reaction mixture was poured onto ice water
extractionThe resulting mixture was then extracted three times with ethyl acetate
washThe combined extracts were washed with saturated sodium chloride aqueous solution
dry with materialAfter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customthe residue was isolated
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-1e07dfb2f64e4e759148679347b1371b
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248772B1

Reaction notes

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