2-Aminoindane → 2,3,4,7-tetrahydro-1H-inden-2-ylamine
Reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[Li]>N>[CH2:3]1[C:4]2[CH2:5][CH:6]=[CH:7][CH2:8][C:9]=2[CH2:10][CH:2]1[NH2:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Liquid ammonia (80 ml) is condensed at −78° C. and 2-aminoindane (2 g, 15 mmol) is added, followed by lithium wire (2 g, 300 mmol) portionwise over 5 minutes. The reaction is stirred at −78° C. for 2 hours, then cautiously quenched with ethanol (100 ml) and warmed to ambient temperature overnight. Water is added, the mixture is extracted with ether and the combined organic extracts are washed with brine, dried (MgSO4) and evaporated to afford 2,3,4,7-tetrahydro-1H-inden-2-ylamine. [M+CH3CN] 177.
Workup
- customcondensed at −78° C.
- customcautiously quenched with ethanol (100 ml)
- temperaturewarmed to ambient temperature overnight
- additionWater is added
- extractionthe mixture is extracted with ether
- washthe combined organic extracts are washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-620c63832b7e4dc5bc80e632159706c9
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745462B2
Reaction notes
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