Triethylamine → HCID 66606755, compound

HRID 554620Notes

Reaction equation

HRID 554620 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:3]=1[CH2:4][NH:5][CH2:6][CH3:7].C(N(CC)CC)C.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:3]=1[CH2:4][N:5]([CH2:6][CH3:7])[C:26]([CH:23]1[CH2:25][CH2:24]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 66603999(2-Bromo-5-trifluoromethyl-benzyl)-ethyl-amine

Product 1

HCID 66606755HCID 66606755, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amine (22.3 g, 79.1 mmol) and triethylamine (16.53 mL, 118.6 mmol) in CH2Cl2 (200 mL) was added cyclopropanecarbonyl chloride (8.68 mL, 94.9 mmol) dropwise over 15 minutes, and the reaction was stirred at room temperature for 2 hours. The mixture was partitioned between CH2Cl2 and H2O, and the aqueous layer was separated and extracted twice with CH2Cl2. The combined organic layers were dried and concentrated, and the residue was purified by silica gel chromatography (10-30% EtOAc in hexanes) to give cyclopropanecarboxylic acid (2-bromo-5-trifluoromethyl-benzyl)-ethyl-amide.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and H2O
  2. customthe aqueous layer was separated
  3. extractionextracted twice with CH2Cl2
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c8f9ef8d207b430b9b76eb0caf48691f
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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