Methanol → N-isopropyl-2,3-dihydro-4-benzofuranamine

HRID 1658279Notes

Reaction equation

HRID 1658279 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([NH2:10])=[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:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[O:1][CH2:2][CH2:3][C:4]=12)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 6362Isopropyl iodideHCID 117010432,3-Dihydro-1-benzofuran-4-amine

Product 1

HCID 21529025N-isopropyl-2,3-dihydro-4-benzofuranamine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 19.7 g. of 2,3-dihydro-4-benzofuranamine in 150 ml. of methanol is added 11 ml. of isopropyliodide and 15.5 ml. of triethylamine. The solution is refluxed for 40 hours and then concentrated in vacuo. The resultant oil is extracted and combined, filtered through Celite, and the ether removed in vacuo to give an oil of N-isopropyl-2,3-dihydro-4-benzofuranamine.

Workup

  1. temperatureThe solution is refluxed for 40 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe resultant oil is extracted
  4. filtrationfiltered through Celite
  5. customthe ether removed in vacuo

Sources & evidence

ORD record
ord-0b4b64c8b02a4d6282d70a2c126bfdba
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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