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

HRID 1785889Notes

Reaction equation

HRID 1785889 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1[CH:29]=[CH:28][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[CH2:11][C@@H:10]2[CH3:27])=[O:8])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)Cl>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([N:19]([C@H:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:30])=[CH:29][CH:28]=3)[C@@H:10]([CH3:27])[CH2:11]2)[C:40](=[O:42])[CH3:41])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 131726427(+/-)-cis-1-(4-Dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-4-(n-4-chlorophenyl)aminoquinoline

Product 1

HCID 58859761(+/-)-cis-n-(4-Chloro-phenyl)-n-[1-(4-dimethylamino-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamideYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-120369491031444abd6f94e7364ffc57
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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