2-Benzofurancarboxamide, N-methyl- → (1-Benzofuran-2-ylmethyl)(methyl)amine

HRID 1920996Notes

Reaction equation

HRID 1920996 reaction equation
B.C1COCC1.[CH3:7][NH:8][C:9]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[CH:15]=1)=O>CO>[CH3:7][NH:8][CH2:9][C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 6603722-Benzofurancarboxamide, N-methyl-HCID 2723981Borane;tetrahydrofuran

Product 1

HCID 5048607(1-Benzofuran-2-ylmethyl)(methyl)amineYield 12.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 M BH3/THF (30 mL, 30 mmole) at 0° C. was added N-methylbenzofuran-2-carboxamide (1.75 g, 10 mmole). The reaction mixture was allowed to warm to RT, then was heated at reflux overnight. The reaction was cooled to 0° C. and excess methanol was added. The resulting solution was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (3% MeOH/CH2Cl2). The tile compound (0.2 g, 12%) was obtained as a white solid: MS (ES) m/e 162 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction was cooled to 0° C.
  4. concentrationThe resulting solution was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on silica gel (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-938d890650e44e3ea401dc3b10fc7ab7
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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