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

HRID 1359540Notes

Reaction equation

HRID 1359540 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-3e1324f37bac45d3b9fe8e4c694a920b
Source dataset
uspto-grants-2003_07
Patent number
US06600058B1

Reaction notes

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