Acetyl chloride → HCID 68921038, compound

HRID 1786083Notes

Reaction equation

HRID 1786083 reaction equation
[CH:1]1([NH:6][C@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C@@H:9]([CH3:27])[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[CH:1]1([N:6]([C@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C@@H:9]([CH3:27])[CH2:8]2)[C:37](=[O:39])[CH3:38])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68923063HCID 68923063, compound

Product 1

HCID 68921038HCID 68921038, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (2S,4R)-N-cyclopentyl-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-amine (100 mg, 02.7 mmol) in methylene chloride (5 mL) was added diisopropylethylamine (120 uL, 0.70 mmol) followed by acetyl chloride (90 uL, 1.27 mmol). The mixture was stirred at r.t. for 4 h. The reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with sat. aqueous sodium bicarbonate, brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford pure N-cyclopentyl-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (100 mg, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with sat. aqueous sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

Sources & evidence

ORD record
ord-cdb556d8e55a4441ab25dc1e72e2e6dd
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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