N-Methylbenzylamine → 2-[Benzyl(methyl)amino]-1-(4-fluorophenyl)ethan-1-one

HRID 1351252Notes

Reaction equation

HRID 1351252 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([N:8]([CH3:9])[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7669N-MethylbenzylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 1202482-Chloro-4'-fluoroacetophenone

Product 1

HCID 144592512-[Benzyl(methyl)amino]-1-(4-fluorophenyl)ethan-1-oneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl-methyl-amine (28.9 g) and triethylamine (33.8 mL) in dimethylformamide (600 mL) was added in 5 portions 2-chloro-1-(4-fluorophenyl)-ethanone (40 g) on an ice bath. After stirring at room temperature for 2 hours, ethyl acetate was added, and the salt that precipitated was removed by filtration, and the filtrate was concentrated. A crude purification was carried out by silica gel column chromatography (hexane/ethyl acetate), and the title compound (56.9 g) was obtained as a colorless oily matter.

Workup

  1. customthe salt that precipitated
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customA crude purification

Sources & evidence

ORD record
ord-5ae767fe029b4d3ab468b43f9e5694cf
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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