Water → 1-(3,4-Dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone

HRID 2409386

Reaction equation

[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[Cl:21])[C:14](=[O:17])[CH2:15]Br.[CH2:22](N(CC)CC)C.[OH2:29]>C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([C:14](=[O:17])[CH2:15][N:2]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:29][CH3:22])[CH:5]=2)[CH3:1])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the above amine (6.2 g, 41.00 mmol) from Step A in methylene chloride (100 mL) was added 3,4-dichlorophenacyl bromide (10.0 g, 37.3 mmol) and the resulting mixture was stirred at 0° C. for 1 Hour prior to the addition of triethylamine (5.20 mL, 37.31 mmol), followed by 1 Hour stirring at 0° C. The reaction mixture was diluted with water (100 mL) then the aqueous phase was extracted with additional methylene chloride (3×75 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated to afford 1-(3,4-dichlorophenyl)-2-((3-methoxybenzyl)(methyl)amino)ethanone (15.08 g) as a light yellow oil, which was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 8.08 (d, J=2.0 Hz, 1H), 7.78 (dd, J=8.5; 2.0 Hz, 1H), 7.50 (d, J=8.5 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 6.90 (d, J=7.5 Hz, 1H), 6.87 (d, J=2.5 Hz, 1H), 6.82 (dd, J=8.0; 2.5 Hz, 1H), 3.79 (s, 3H), 3.66 (s, 2H), 3.60 (s, 2H), 2.33 (s, 3H).

Workup

stirringstirring at 0° C
extractionthe aqueous phase was extracted with additional methylene chloride (3×75 mL)
dry with materialThe combined extracts were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-183c3d6a3c96446d8f601fabe7295283
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815894B2

Linked notes

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