Acetyl chloride → HCID 17773231, compound

HRID 635326Notes

Reaction equation

HRID 635326 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[C:25]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=4[NH:19][CH:18]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:33]([N:19]1[C:20]2[CH2:21][CH2:22][CH2:23][CH2:24][C:25]=2[C:17]([CH2:16][CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:18]1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 17773253HCID 17773253, compound

Product 1

HCID 17773231HCID 17773231, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-(4-(4-Chlorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydroindole (0.5 g) obtained in Example 161 and triethylamine (0.6 ml) were dissolved in dichloromethane (10 ml) and acetyl chloride (0.3 g) was added under ice-cooling with stirring. The reaction mixture was stirred for 2 hours at room temperature and an aqueous potassium carbonate solution is added, and the chloroform layer was separated. After drying over magnesium sulfate, the solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography to give 1-acetyl-3-(3-(4-(4chlorophenyl)piperazin-1-yl)propyl)-4,5,6,7-tetrahydroindole.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 2 hours at room temperature
  3. customthe chloroform layer was separated
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-acaf6a60582d42df8570536b066bf716
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

Loading…