Methylamine → N-Methyl-1-(quinoxalin-2-yl)methanamine

HRID 1091083Notes

Reaction equation

HRID 1091083 reaction equation
Br[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:13][NH2:14]>C(O)C>[CH3:13][NH:14][CH2:2][C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 52877592-(Bromomethyl)quinoxaline

Product 1

HCID 15675889N-Methyl-1-(quinoxalin-2-yl)methanamineYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The 2-(bromomethyl)quinoxaline (3.0 g, 13.4 mmol) was added portionwise to a stirring solution of methylamine (30%) in ethanol (100 mL) at 0° C. The reaction was stirred at 0° C. for 2 hours, concentrated, and partitioned between 10% aqueous potassium carbonate/ethyl acetate. The organic phase was dried (MgSO4), decolorized (charcoal) and concentrated. Purification was accomplished by eluting the sample through a short silica plug to yield 1.80 g (78%) of a brown oil.

Workup

  1. concentrationconcentrated
  2. custompartitioned between 10% aqueous potassium carbonate/ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification
  6. washby eluting the sample through a short silica plug

Sources & evidence

ORD record
ord-fd9897845b794d08a0291762afa592f9
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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