Bromomethyl 4-methoxyphenyl ketone → HCID 16753664, compound

HRID 397065Notes

Reaction equation

HRID 397065 reaction equation
CCN(CC)CC.[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:19]>C1COCC1>[CH2:8]([NH:15][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 7504BenzylamineHCID 8471Triethylamine

Product 1

HCID 16753664HCID 16753664, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Et3N (13.55 g, 133.9 mmol) and benzylamine (11.96 g, 111.6 mmol) in THF (25 ml) was added 2-bromo-1-(4-methoxy-phenyl)-ethanone (25.56 g, 111.6 mmol). The reaction was stirred at RT for 60 minutes, then filtered and the filtrate concentrated in vacuo. The residue was purified via flash chromatography (SiO2, gradient column 35% to 80% EtOAc/hexanes) to give the title product (17.12 g, 67.0 mmol, 60% yield).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified via flash chromatography (SiO2, gradient column 35% to 80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ed0e479273984845b8439adacff4fa2e
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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