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

HRID 1451788Notes

Reaction equation

HRID 1451788 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([NH:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)(=O)[CH2:8][CH3:9].[Cl-].[NH4+]>O1CCCC1>[CH2:7]([NH:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11701165Propanamide, N-(2,3-dihydro-1H-inden-2-yl)-HCID 21226445Aluminium lithium hydride2×

Product 1

HCID 17221237N-propyl-2,3-dihydro-1H-inden-2-amineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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

Workup

  1. additionwas added dropwise to the suspension
  2. temperatureThe mixture was refluxed
  3. temperatureunder heating for 2 hours
  4. temperatureAfter cooling
  5. customwere removed by filtration
  6. concentrationThe filtrate was concentrated
  7. additionchloroform was added to the residue
  8. washThe mixture was washed with water
  9. customdried
  10. customthe solvent was removed

Sources & evidence

ORD record
ord-4e143339c7734a54bc1b1ec7e7710727
Source dataset
uspto-grants-1997_02
Patent number
US05605901

Reaction notes

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