Acetyl chloride → HCID 22038240, compound

HRID 1790528Notes

Reaction equation

HRID 1790528 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:32])[C:14]2[C:9](=[CH:10][C:11]([CH2:15][NH2:16])=[CH:12][CH:13]=2)[N:8]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH2:19][CH2:18]2)[CH2:7]1.C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[CH3:5][C:6]1([CH3:32])[C:14]2[C:9](=[CH:10][C:11]([CH2:15][NH:16][C:1](=[O:3])[CH3:2])=[CH:12][CH:13]=2)[N:8]([CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)[CH2:19][CH2:18]2)[CH2:7]1

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22037950HCID 22037950, compound

Product 1

HCID 22038240HCID 22038240, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, acetyl chloride (0.05 ml) was added dropwise into a solution of 3,3-dimethyl-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (0.22 g) obtained above and triethylamine (0.5 ml) in tetrahydrofuran (10 ml) and the resultant mixture was stirred at room temperature for 1 hr. Then a 1 N aqueous solution (5 ml) of sodium hydroxide and water (10 ml) were added to the reaction mixture, which was extracted with ethyl acetate, washed with brine and dried over magnesium sulfate. After evaporating the solvent, the residue was purified by silica gel column chromatography (chloroform/methanol system) and crystallized from ethyl acetate/hexane to give the title compound (0.18 g) as a yellowish white powder (yield: 73.7%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol system)
  6. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-271189629c0649539b8aa11b42376277
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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