Methylamine → HCID 66817020, compound

HRID 1754976Notes

Reaction equation

HRID 1754976 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH2:11]I)=[CH:6][C:5]=1[CH3:13]>CN(C=O)C>[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH2:11][NH:2][CH3:1])=[CH:6][C:5]=1[CH3:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 66817591HCID 66817591, compound

Product 1

HCID 66817020HCID 66817020, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylamine (12.3 ml, 24.60 mmol, 2.0 M solution in methanol) was added dropwise to a solution of 2-bromo-5-iodomethyl-1,3-dimethyl-benzene (400 mg, 1.23 mmol) in anhydrous DMF (12 ml), and the mixture was stirred at room temperature for two days. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The organic layer was then sequentially washed with water and saturated brine and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 1-(4-bromo-3,5-dimethylphenyl)-N-methylmethanamine (280 mg, 100%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was then sequentially washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-745383d9031748baae835cfaf7039a38
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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