N-Methylbenzylamine → N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamine

HRID 2063824Notes

Reaction equation

HRID 2063824 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].CC(N(C)C)=O.I[CH2:23][C:24]1([CH3:36])[CH2:28][C:27]2[C:29]([CH3:35])=[CH:30][C:31]([CH3:34])=[C:32]([CH3:33])[C:26]=2[O:25]1>C(OCC)(=O)C.O>[CH3:1][N:2]([CH2:23][C:24]1([CH3:36])[CH2:28][C:27]2[C:29]([CH3:35])=[CH:30][C:31]([CH3:34])=[C:32]([CH3:33])[C:26]=2[O:25]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 152683052-(Iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran

Product 1

HCID 66760229N-methyl-1-phenyl-N-[(2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl)methyl]methanamineYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-methylbenzylamine (766 mg, 3.16 mmol) and potassium carbonate (1.09 g, 7.90 mmol) were added to a solution of DMA (5 mL) containing 2-(iodomethyl)-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran (1.00 g, 3.16 mmol) synthesized in Reference Example 126, and the mixture was stirred under heated reflux for 4 hours. The reaction solution was cooled to room temperature, and water and ethyl acetate were added thereto to separate an organic layer. The organic layer was washed with water and saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-93:7) to give 730 mg of the title compound (yield: 75%).

Workup

  1. customsynthesized in Reference Example 126
  2. temperatureunder heated
  3. temperaturereflux for 4 hours
  4. customto separate an organic layer
  5. washThe organic layer was washed with water and saturated saline
  6. customdried
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-93:7)

Sources & evidence

ORD record
ord-8c4d5d476906495d815bd295bbc14b3b
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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