Lithium → 5,6-diethyl-2,3,4,7-tetrahydro-1H-inden-2-ylamine

HRID 19724

Reaction equation

HRID 19724 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH2:13][CH3:14])=[C:7]([CH2:11][CH3:12])[CH:8]=2)[CH2:3]1.[Li]>N>[CH2:11]([C:7]1[CH2:8][C:9]2[CH2:10][CH:2]([NH2:1])[CH2:3][C:4]=2[CH2:5][C:6]=1[CH2:13][CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 101926155,6-diethyl-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 685613735,6-diethyl-2,3,4,7-tetrahydro-1H-inden-2-ylamine

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
-78 °C

Procedure

Liquid ammonia (50 ml) is condensed at −78° C. and 2-amino-5,6-diethylindane (WO 0075114; 1 g, 4.43 mmol) is added, followed by lithium wire (0.615 g, 88 mmol) portionwise over 5 minutes. The reaction is stirred at −78° C. for 3 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 5,6-diethyl-2,3,4,7-tetrahydro-1H-inden-2-ylamine. δH 0.95 (t J 7.3 6H), 1.95-2.10 (m 2H), 2.08 (q J 4H), 2.6 (m 6H), 3.65 (m 1H)

Workup

  1. customcondensed at −78° C.
  2. customcautiously quenched with ethanol (100 ml)
  3. temperaturewarmed to ambient temperature overnight
  4. additionWater is added
  5. extractionthe mixture is extracted with ether
  6. washthe combined organic extracts are washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-56eff91f14b840659d7b5118e7bb3b88
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Linked notes

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