Aluminium lithium hydride → HCID 44541735, compound

HRID 1716803Notes

Reaction equation

HRID 1716803 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:10]#[N:11])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][NH:12][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][NH2:11])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68426881HCID 68426881, compound

Product 1

HCID 44541735HCID 44541735, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

The crude (4-methoxyphenyl)-[2-(4-methoxyphenyl)ethylamino]-acetonitrile obtained in the above procedure is dissolved in diethyl ether (20 mL) and this solution is slowly added to an ice-cold solution of lithium aluminum hydride (1.0M, 16 mL, 16 mmol) in diethyl ether. The cooling bath is removed and the solution is allowed to stir for 1 hour. The reaction solution is then re-cooled to 5° C. and water (4 mL) is added, followed by 3N NaOH (3 mL). The ether is then decanted from the resulting solid and the solid is again washed with diethyl ether (20 mL). The combined ether washings are dried (Na2SO4) and concentrated in vacuo to afford 2.5 g (quantitative yield) of the desired compound. MS (301) (MH+).

Workup

  1. customThe cooling bath is removed
  2. additionwater (4 mL) is added
  3. customThe ether is then decanted from the resulting solid
  4. washthe solid is again washed with diethyl ether (20 mL)
  5. dry with materialThe combined ether washings are dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d275c3f6de53440d9dae5fa6ecb031d7
Source dataset
uspto-grants-2010_09
Patent number
US07803827B2

Reaction notes

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