Aluminium lithium hydride → Benzyl-(5,6-diethyl-indan-2-yl)-amine

HRID 1162378Notes

Reaction equation

HRID 1162378 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6]2)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:15]([NH:14][CH:7]1[CH2:8][C:9]2[C:5](=[CH:4][C:3]([CH2:1][CH3:2])=[C:11]([CH2:12][CH3:13])[CH:10]=2)[CH2:6]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22499179N-(5,6-Diethyl-indan-2-yl)-benzamide

Product 1

HCID 22499194Benzyl-(5,6-diethyl-indan-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

N-(5,6-Diethyl-indan-2-yl)-benzamide (3.30 g) is dissolved in dry THF (100 mL). Lithium aluminium hydride, 1M in THF (22.52 ml) is then added dropwise. The reaction mixture is stirred at 50° C. The reaction is shown to be complete by TLC after 6 hours. The reaction mixture is allowed to cool, poured slowly into ice-water (200 mL) and extracted with diethyl ether (2×105 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The product is not purified further. TLC (silica, n-hexane/ethyl acetate 2:1 Rf=0.20).

Workup

  1. temperatureto cool
  2. extractionextracted with diethyl ether (2×105 mL)
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed in vacuo
  6. customThe product is not purified further

Sources & evidence

ORD record
ord-b7d00e5931b04a5caff473228c6cf4df
Source dataset
uspto-grants-2010_10
Patent number
US07820694B2

Reaction notes

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