Methanol → N-isopropyl-2,3-dihydro-5-benzofuranamine

HRID 1658282Notes

Reaction equation

HRID 1658282 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[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:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 6362Isopropyl iodideHCID 38411022,3-Dihydro-1-benzofuran-5-amine

Product 1

HCID 21529005N-isopropyl-2,3-dihydro-5-benzofuranamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 40 g. of 2,3-dihydro-5-benzofuranamine in 200 ml. of methanol is added 23 ml. of isopropyl iodide and 35 ml. of triethylamine. The solution is refluxed for 55 hours and then concentrated in vacuo. The resultant oil is extracted several times with diethyl ether, the extract combined, filtered through Celite, and the ether removed in vacuo to obtain an oil of N-isopropyl-2,3-dihydro-5-benzofuranamine.

Workup

  1. temperatureThe solution is refluxed for 55 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe resultant oil is extracted several times with diethyl ether
  4. filtrationfiltered through Celite
  5. customthe ether removed in vacuo

Sources & evidence

ORD record
ord-65890563b24a43c99e67fda64e4e1a72
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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