Potassium Carbonate → HCID 66857182, compound

HRID 2037495Notes

Reaction equation

HRID 2037495 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][CH2:11][CH2:12][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH3:9])=[CH:4][CH:3]=1.[C:18]([O-:21])([O-])=[O:19].[K+].[K+].Cl[C:25]([O-])=O>C(Cl)Cl>[CH3:25][O:21][C:18](=[O:19])[N:10]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:9])[CH2:11][CH2:12][C:13](=[O:17])[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21226386CarbonochloridateHCID 66600763HCID 66600763, compound

Product 1

HCID 66857182HCID 66857182, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[1-(4-bromo-phenyl)-ethylamino]-4-methyl-pentan-3-one (3.42 g, 0.01 mol) and K2CO3 (6.9 g, 0.05 mol) in dried CH2Cl2 (50 mL) was added chloroformate (1.41 g, 0.015 mol). The mixture was refluxed overnight. The solvent was removed to give the crude product, which was purified by column to give [1-(4-bromo-phenyl)-ethyl]-(4-methyl-3-oxo-pentyl)-carbamic acid methyl ester (2.8 g, 79%). 1H NMR (CDCl3): 1.01 (m, 6H), 1.48 (m, 3H), 2.25-2.47 (m, 2H), 2.62 (m, 1H), 3.24 (m, 2H), 5.46 (s, 1H), 7.17 (m, 2H), 7.45 (m, 2H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe solvent was removed
  3. customto give the crude product, which
  4. customwas purified by column

Sources & evidence

ORD record
ord-a674df69ee854604a06e87617388c9d0
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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