Aluminium lithium hydride → HCID 44541735, compound

HRID 1785605Notes

Reaction equation

HRID 1785605 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-9e49041f207c48428e64c3482fdb574c
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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