Triethylamine → 1-bromo-N-(2-oxopentyl)-cyclopropane-1-carbamide

HRID 1166608Notes

Reaction equation

HRID 1166608 reaction equation
[Br:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.Cl.[NH2:9][CH2:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14].C1(N=C=NC2CCCCC2)CCCCC1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1([C:5]([NH:9][CH2:10][C:11](=[O:15])[CH2:12][CH2:13][CH3:14])=[O:7])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 125517611-Aminopentan-2-one hydrochlorideHCID 128674801-Bromocyclopropane-1-carboxylic acid

Product 1

HCID 180009151-bromo-N-(2-oxopentyl)-cyclopropane-1-carbamideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.57 g of 1-bromocyclopropanecarboxylic acid 4 [H. M. R. Hoffmann et al. J. org. Chem. 54, 6096 (1989)], 2.22 g of 1-amino-2-pentanone hydrochloride 5 [M. Jackman et al. J. Am. Chem. Soc. 70, 2884 (1948)] and 3.36 g of N,N′-dicyclohexylcarbodiimide in 234 ml of methylene chloride in the presence of 2.46 ml of triethylamine is stirred overnight at room temperature. Then, it is filtered, the filtrate is concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate/hexane. 2.74 g of 1-bromo-N-(2-oxopentyl)-cyclopropane-1-carbamide 6 is obtained as a crystallizing oil.

Workup

  1. filtrationThen, it is filtered
  2. concentrationthe filtrate is concentrated by evaporation
  3. customthe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1fab3457ae2f40fba59e070b2e1b8d01
Source dataset
uspto-grants-2003_09
Patent number
US06613920B1

Reaction notes

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