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

HRID 1349353Notes

Reaction equation

HRID 1349353 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-0d631c31c0fc404dabf8b781a9ef1f24
Source dataset
uspto-grants-2007_05
Patent number
US07211680B2

Reaction notes

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