Acetyl chloride → HCID 22038395, compound

HRID 1790407Notes

Reaction equation

HRID 1790407 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:25](Cl)(=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:23][CH:24]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 22038128HCID 22038128, compound

Product 1

HCID 22038395HCID 22038395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[1-(4-Aminophenethyl)piperidin-4-yl]indoline (310 mg) was dissolved in methylene chloride (3 ml). Under ice cooling, acetyl chloride (0.103 ml) was added to the resultant solution followed by stirring the obtained mixture for 45 min. After adding a 10% aqueous solution of potassium carbonate, the reaction solution was extracted with ethyl acetate. Then the organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the resulting residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (200 mg) as an oil.

Workup

  1. extractionthe reaction solution was extracted with ethyl acetate
  2. washThen the organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe resulting residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-de6d8003fadc47fbb3111aa40970f83a
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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