Acetic Acid → (1-Benzofuran-2-ylmethyl)(methyl)amine

HRID 1297427Notes

Reaction equation

HRID 1297427 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.CN.CC(O)=O.[BH3-][C:19]#[N:20].[Na+]>CO>[CH3:19][NH:20][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 613412-BenzofurancarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 5048607(1-Benzofuran-2-ylmethyl)(methyl)amineYield 50.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2-benzofurancarboxaldehyde (2.22 g, 15.2 mmole) in MeOH (5 mL) was added 2 M methylamine in MeOH (15 mL), HOAc (0.86 mL, 15 mmole), and NaBH3CN (1.0 g, 15.9 mmole). The reaction was stirred for 18 h at RT then concentrated under vacuum. The remaining residue was taken up in Et2O, and the solution was washed with 1 N NaOH then brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography on silica gel (5% (5% NH4OH in MeOH)/CHCl3) gave the title compound (1.23 g, 50%) as a pale yellow oil: MS (ES) m/e 162.4 (M+H)+.

Workup

  1. concentrationthen concentrated under vacuum
  2. washthe solution was washed with 1 N NaOH
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography on silica gel (5% (5% NH4OH in MeOH)/CHCl3)

Sources & evidence

ORD record
ord-ecbb58f9fc844d17911fbadbb4254d4a
Source dataset
uspto-grants-2007_07
Patent number
US07250424B2

Reaction notes

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