Chloroacetyl chloride → HCID 17985641, compound

HRID 557194Notes

Reaction equation

HRID 557194 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(C(C)C)CC)(C)C.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24][NH:25][CH2:26][CH2:27][CH3:28])[CH:17]=[CH:16]1>C(Cl)Cl>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24][N:25]([CH2:26][CH2:27][CH3:28])[C:3](=[O:4])[CH2:2][Cl:1])[CH:17]=[CH:16]1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 62998053HCID 62998053, compound

Product 1

HCID 17985641HCID 17985641, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add chloroacetyl chloride (1.7 ml, 21.71 mmol) and diisopropylethylamine (10.38 ml, 62.04 mmol) to a solution of (1H-Indol-7-ylmethyl)propylamine (3.89 g, 20.68 mmol) in methylene chloride. Stir for 2 hours, quench with saturated aqueous ammonium chloride and extract into ethyl acetate. Wash the organic layers with saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure to yield N-(1H-indol-7-yl)methyl N-propyl 2-chloroacetamide (5.47 gm, 20.68 mMol).

Workup

  1. customquench with saturated aqueous ammonium chloride
  2. extractionextract into ethyl acetate
  3. washWash the organic layers with saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-55c596676b8e4777a4f755f0610883df
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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