Cyclopropanecarbonyl chloride → N-(4-bromobenzyl)cyclopropanecarboxamide

HRID 1865865Notes

Reaction equation

HRID 1865865 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[CH:20]1([C:23](Cl)=[O:24])[CH2:22][CH2:21]1>ClCCl>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:23]([CH:20]2[CH2:22][CH2:21]2)=[O:24])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 27240964-Bromobenzylamine hydrochloride

Product 1

HCID 61400450N-(4-bromobenzyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-benzylamine hydrochloride (367.8 mg, 1.7 mmol) was dissolved in dichloromethane (15 mL), and the solution was cooled to 0° C. DIEA (380 μL, 2.2 mmol) was then added, and the reaction was stirred at 0° C. for 5 minutes. Then cyclopropanecarbonyl chloride (180 μL, 2.3 mmol) was added, and the reaction was stirred at 0° C. for 20 minutes. The reaction was quenched with distilled water, and the solvents were removed. The resulting mixture was redissolved in DMF (10 mL) and purified by reverse phase HPLC to give the desired product.

Workup

  1. stirringthe reaction was stirred at 0° C. for 20 minutes
  2. customThe reaction was quenched with distilled water
  3. customthe solvents were removed
  4. dissolutionThe resulting mixture was redissolved in DMF (10 mL)
  5. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-0d6614e9d7a64813a0212924a8ef14dc
Source dataset
uspto-grants-2009_12
Patent number
US07629340B2

Reaction notes

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