Water → N-Methylindan-2-amine

HRID 1531283Notes

Reaction equation

HRID 1531283 reaction equation
C(O[C:4]([NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O)C.C(=O)(O)N.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>CCOCC>[CH3:4][NH:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21253362Carbamate 2-(ethoxycarbonyl-amino)indane

Product 1

HCID 15023225N-Methylindan-2-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of the carbamate 2-(ethoxycarbonyl-amino)indane (6.07 g, 29.6 mmol) in Et2O (100 mL) is added slowly to a mixture of LiAlH4 (1.70 g, 44.7 mmol) in Et2O (100 ml) chilled at 0°. The resulting mixture is stirred for 18 h and allowed to warm to 20°. The reaction mixture is re-chilled to 0° and treated cautiously with H2O (1.7 mL), 15% NaOH (1.7 mL) and again H2O (5.1 mL). The mixture is stirred for 20 minutes, warming slowly to 20°. The precipitate is vacuum filtered and the filtrate extracted into 1N HCl. The acid solution is washed with fresh Et2O, then basified with cold 1N NaOH. The cloudy mixture is extracted with Et2O, washed with saturated brine, dried over Na2SO4, is filtered and concentrated to an oil.

Workup

  1. temperaturechilled at 0°
  2. temperatureto warm to 20°
  3. temperatureThe reaction mixture is re-chilled to 0°
  4. stirringThe mixture is stirred for 20 minutes
  5. temperaturewarming slowly to 20°
  6. filtrationfiltered
  7. extractionthe filtrate extracted into 1N HCl
  8. washThe acid solution is washed with fresh Et2O
  9. extractionThe cloudy mixture is extracted with Et2O
  10. washwashed with saturated brine
  11. dry with materialdried over Na2SO4
  12. filtrationis filtered
  13. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-e81d0e3be9934d94842c5994466059d5
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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