Acetyl chloride → N-(3-Bromobenzyl)-N-methylacetamide

HRID 561785

Reaction equation

HRID 561785 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][NH:6][CH3:7].CCN(C(C)C)C(C)C.[C:20](Cl)(=[O:22])[CH3:21]>CN(C)C1C=CN=CC=1.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][N:6]([CH3:7])[C:20](=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 457588Benzenemethanamine, 3-bromo-N-methyl-

Product 1

HCID 57956102N-(3-Bromobenzyl)-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a DMF (0.1 M) solution of 3-bromo-N-methylbenzylamine (1 eq.), Hunig's base (3 eq) and 4-(dimethylamino)pyridine (5% loading) was added acetyl chloride (1.5 eq). The resulting reaction mixture was stirred at RT for 16 h. After quenching the reaction with sat. aq. NaHCO3, the mixture was extracted with EtOAc. The organic extract was washed with 10% aq. HCl, sat. aq. NaHCO3, and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a yellow oil. Purification by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with sat. aq. NaHCO3
  4. extractionthe mixture was extracted with EtOAc
  5. extractionThe organic extract
  6. washwas washed with 10% aq. HCl, sat. aq. NaHCO3, and brine
  7. dry with materialDrying over Na2SO4, filtration and concentration of the filtrate in vacuo
  8. customafforded the crude product as a yellow oil
  9. customPurification by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-249c480083964669afc97ff8a33b281e
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Linked notes

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