Acetyl chloride → (+/-)-cis-n-(4-Chloro-phenyl)-n-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide

To a solution of (±)-cis-1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(N-4-chlorophenyl)aminoquinoline (120 mg, 0.29 mmol) in methylene chloride (2 mL) was added diisopropylethylamine (37 mg, 0.051 mL, 0.29 mmol) followed by acetyl chloride (2 mL). The mixture was stirred at rt 4 h. The mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with sat. aqueous sodium bicarbonate, brine and dried over sodium sulfate. The drying agent was removed by filtration under reduced pressure, concentrated and purified by silica gel chromatography (100% hexanes-25/75 hexanes/ethyl acetate gradient) to afford pure (±)-cis-N-(4-chloro-phenyl)-N-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (45 mg, 34%).

1. concentrationThe mixture was concentrated under reduced pressure
2. dissolutiondissolved in ethyl acetate
3. washwashed with sat. aqueous sodium bicarbonate, brine
4. dry with materialdried over sodium sulfate
5. customThe drying agent was removed by filtration under reduced pressure
6. concentrationconcentrated
7. custompurified by silica gel chromatography (100% hexanes-25/75 hexanes/ethyl acetate gradient)

ORD 기록

ord-120369491031444abd6f94e7364ffc57

출처 데이터셋

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07504508B2