Methanol → N-isopropyl-2,3-dihydro-6-benzofuranamine

HRID 1658285Notes

Reaction equation

HRID 1658285 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CO.[CH:13](I)([CH3:15])[CH3:14]>C(N(CC)CC)C>[CH:13]([NH:10][C:7]1[CH:8]=[CH:9][C:4]2[CH2:3][CH2:2][O:1][C:5]=2[CH:6]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 6362Isopropyl iodideHCID 123690442,3-Dihydro-1-benzofuran-6-amine

Product 1

HCID 21528943N-isopropyl-2,3-dihydro-6-benzofuranamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 2.8 g. of 2,3-dihydro-6-benzofuranamine in 150 ml. of methanol is added 18 ml. of isopropyl iodide and 26.5 ml. of triethylamine. The solution is refluxed for 60 hours and then concentrated in vacuo. The resultant oil is extracted repeatedly with diethyl ether. The extracts are combined, filtered through Celite, and the ether removed in vacuo to give an oil of N-isopropyl-2,3-dihydro-6-benzofuranamine.

Workup

  1. temperatureThe solution is refluxed for 60 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe resultant oil is extracted repeatedly with diethyl ether
  4. filtrationfiltered through Celite
  5. customthe ether removed in vacuo

Sources & evidence

ORD record
ord-a51d9ac27980474b8dd4ba0d8f526425
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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