Dimethylamine → N-(2-Methoxyphenyl)-4-dimethylaminomethylbenzamide

HRID 2454

Reaction equation

Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:8])=[CH:5][CH:4]=1.[CH3:20][NH:21][CH3:22]>O1CCOCC1>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([CH2:2][N:21]([CH3:22])[CH3:20])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In an atmosphere of argon, 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) was put into a 25 ml capacity eggplant type flask equipped with a cold finger and dissolved in dioxane (3 ml), followed by the addition of 50% dimethylamine aqueous solution (3 ml) at room temperature. After 2.5 hours of stirring at 80° C. and subsequent removal of dioxane by evaporation, the resulting residue was diluted with ethyl acetate (30 ml). The thus diluted solution was dried on anhydrous sodium carbonate, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether-ethyl acetate-ethyl acetate:methanol=10:1) to obtain 284 mg (100%) of the title compound in the form of colorless oil.

Workup

customequipped with a cold finger
customsubsequent removal of dioxane
customby evaporation
additionthe resulting residue was diluted with ethyl acetate (30 ml)
dry with materialThe thus diluted solution was dried on anhydrous sodium carbonate
customthe resulting residue was purified

Sources & evidence

ORD record: ord-e6f09e6358c645c8a45e3f4af446ce3d
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Linked notes

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