Methylamine → (1-Benzofuran-2-ylmethyl)(methyl)amine

HRID 1091080Notes

Reaction equation

HRID 1091080 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1.[CH3:12][NH2:13]>O>[CH3:12][NH:13][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1843482-Chloromethylbenzofuran

Product 1

HCID 5048607(1-Benzofuran-2-ylmethyl)(methyl)amineYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Chloromethyl) benzofuran (2.77 g, 16.63 mmol) was dissolved in aqueous methylamine (40 mL, 40 wt % in H2O) at 10° C. under a nitrogen atmosphere. After 10 minutes, the reaction mixture was warmed to room temperature and stirring was continued for 72 hours. The mixture was diluted with water and extracted with dichloromethane. The organic phase was dried (MgSO4) and concentrated to afford crude product which was purified by flash column chromatography (10% methanol/dichloromethane) to afford 1.00 g (37%) of pure product as a pale yellow oil.

Workup

  1. waitwas continued for 72 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by flash column chromatography (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-a25a6ee593234ba0b5717a837ad859fb
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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