Tetrahydrofuran → N-propyl-2,3-dihydro-1H-inden-2-amine

HRID 1598564Notes

Reaction equation

HRID 1598564 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1N)(=O)CC.[Cl-].[NH4+:22].O1C[CH2:26][CH2:25][CH2:24]1>>[CH2:24]([NH:22][CH:11]1[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19]1)[CH2:25][CH3:26]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydride2×HCID 543218082-Propionyl aminoindane

Product 1

HCID 17221237N-propyl-2,3-dihydro-1H-inden-2-amine

Procedure

In 100 ml of tetrahydrofuran was suspended 5.7 g of lithium aluminum hydride, and to the suspension was added dropwise 18.9 g of 2-propionyl aminoindane dissolved in 150 ml of tetrahydrofuran. The mixture was refluxed under heating for 2 hours. After cooling, excessive lithium aluminum hydride was treated with a saturated ammonium chloride aqueous solution, and insolubles were removed by filtration. The filtrate was condensed, and chloroform was added to the residue. After the mixture was washed with 10 water and dried, the solvent was removed to obtain 17.5 g of 2-propylaminoindane.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. temperatureAfter cooling
  4. customwere removed by filtration
  5. customcondensed, and chloroform
  6. additionwas added to the residue
  7. washAfter the mixture was washed with 10 water
  8. customdried
  9. customthe solvent was removed

Sources & evidence

ORD record
ord-968c44bf8df84e558d1424ad845337e4
Source dataset
uspto-grants-1998_04
Patent number
US05739132

Reaction notes

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