Methanol → N-isopropyl-2,3-dihydro-7-benzofuranamine

HRID 1658289Notes

Reaction equation

HRID 1658289 reaction equation
[O:1]1[C:5]2[C:6]([NH2:10])=[CH:7][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:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 6362Isopropyl iodideHCID 128059502,3-Dihydro-1-benzofuran-7-amine

Product 1

HCID 21528960N-isopropyl-2,3-dihydro-7-benzofuranamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 15 g. of 2,3-dihydro-7-benzofuranamine in 150 ml. of methanol is added 8.5 ml. of isopropyl iodide and 13.4 ml. of triethylamine. The solution is refluxed for 45 hours and then concentrated in vacuo. The resulting oil is extracted several times with diethyl ether, the ether extracted combined filtered through Celite, and the ether removed in vacuo to obtain an oil of N-isopropyl-2,3-dihydro-7-benzofuranamine.

Workup

  1. temperatureThe solution is refluxed for 45 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe resulting oil is extracted several times with diethyl ether
  4. extractionthe ether extracted
  5. filtrationcombined filtered through Celite
  6. customthe ether removed in vacuo

Sources & evidence

ORD record
ord-a1faca4a36954c76af9ae6b1b10ea945
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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