Acetyl chloride → HCID 21270102, compound

HRID 1194394Notes

Reaction equation

HRID 1194394 reaction equation
Cl.CN(CC[CH2:7][NH:8][C:9]([C:11]1[N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])C.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28].[C:34]([Cl:37])(=[O:36])[CH3:35]>ClCCl>[ClH:37].[CH2:27]([N:29]([CH2:32][CH2:33][CH2:7][NH:8][C:9]([C:11]1[N:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[C:18]([C:19]=1[O:20][C:34](=[O:36])[CH3:35])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:30][CH3:31])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54724115HCID 54724115, compound

Product 1

HCID 21270102HCID 21270102, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.66 g of 2-[3-(N,N-dimethylamino)propylaminocarbonyl]-3-hydroxy-1-phenylindole hydrochloride are dissolved in 25 ml dichloromethane and mixed successively under vigorous agitation with 0.6 ml of triethylamine and 0.3 ml of acetyl chloride. The reaction mixture is boiled for 30 min under reflux. After cooling, the mixture is washed with a small amount of a saturated solution of sodium chloride, the organic phase dried over sodium sulfate and evaporated under vacuum. Following recrystallization from isopropanol, 1.00 g (57% of theoretical) 2[3-(N,N-diethylamino)-propylaminocarbonyl]-3-acetoxy-1-phenylindole hydrochloride is obtained. Melting point: 174°-176° C.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. washthe mixture is washed with a small amount of a saturated solution of sodium chloride
  4. dry with materialthe organic phase dried over sodium sulfate
  5. customevaporated under vacuum
  6. customrecrystallization from isopropanol

Sources & evidence

ORD record
ord-0c5fa10195fa4972879b9f20f9ba0006
Source dataset
uspto-grants-1989_03
Patent number
US04814345

Reaction notes

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