Methylamine → 2-Bromo-N-methylbenzylamine

HRID 1358503Notes

Reaction equation

HRID 1358503 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:10]N>CO.C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][CH3:10]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 3340722-Bromobenzylamine

Product 1

HCID 5223602-Bromo-N-methylbenzylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-bromobenzylamine (9 g, 36.1 mmol) in MeOH (60 ml) was added dropwise over 30 min. to a solution of methylamine in MeOH (200 mL of a 2.0 M solution, 0.4 mol). The resulting solution was stirred at rt for 2 h and concentrated. The residue obtained was dissolved in DCM (100 mL) and successively washed with saturated aqueous sodium carbonate, dried over sodium sulphate, and concentrated. The resulting oil was distilled to afford the title compound (7 g, 95%) as a colorless oil (b.p. 110° C. at 0.1 mm Hg, LC/MS retention time=1.22 min.; M+=201.92 Column: Phenominex 4.6 mm×50 mm. Solvent A=10% MeOH, 90% H2O, 10 mM NH4Ac; Solvent B=90% MeOH, 10% H2O, 10 nM NH4Ac, Flow rate: 4 mL/min, Gradient: 0% B-100% B 4 min.).

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. washsuccessively washed with saturated aqueous sodium carbonate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. distillationThe resulting oil was distilled

Sources & evidence

ORD record
ord-7897891164ec4f8a8d7515520a218b6f
Source dataset
uspto-grants-2003_07
Patent number
US06596747B2

Reaction notes

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