Methylamine → (3-Ethyl-benzofuran-2-ylmethyl)methylamine

HRID 2097060Notes

Reaction equation

HRID 2097060 reaction equation
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]=O)[CH3:2].[CH3:14][NH2:15].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][NH:15][CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 126115243-Ethyl-1-benzofuran-2-carbaldehyde

Product 1

HCID 59277558(3-Ethyl-benzofuran-2-ylmethyl)methylamineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Ethyl-benzofuran-2-carbaldehyde (1.16 g, 6.65 mmol) was added to a solution of methylamine (26 mL of a 2M solution in MeOH, 52 mmol) and the resulting mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was taken up in ethanol (20 mL) and then cooled in an ice-bath. NaBH4 (370 mg, 9.90 mmol) was added in one portion. The mixture was concentrated under reduced pressure and the residue taken up in 1 M NaOH. The mixture was extracted with Et2O (3×). The combined organics were washed with brine, dried and concentrated under reduced pressure to give the title compound (1.12 g, 89%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.58 (dd, J=8.4, 6.6 Hz, 1H), 7.46 (d, J=7.2 Hz, 1H), 7.30-7.25 (m, 2H), 3.75 (s, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.26 (s, 3H), 2.05 (br s, 1H), 1.21 (t, J=7.5 Hz, 3H); ESI MS m/z 190 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. temperaturecooled in an ice-bath
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionThe mixture was extracted with Et2O (3×)
  5. washThe combined organics were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9dc8d7044ba24b45bd878117a9d46436
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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