Aluminium lithium hydride → HCID 59300191, compound

HRID 2236484Notes

Reaction equation

HRID 2236484 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=2[O:19][CH2:20][O:21][CH3:22])[CH:8]=[CH:9][CH:10]=1)[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][C:12]=2[O:19][CH2:20][O:21][CH3:22])[CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68695387HCID 68695387, compound

Product 1

HCID 59300191HCID 59300191, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3′-Dimethylaminomethyl-2-methoxymethoxy-biphenyl-4-carbonitrile (crude material from above) is dissolved in ether (10 mL). The resulting solution is slowly added to a suspension of LiAlH4 (100 mg, 2.6 mmol) in Et2O. After addition, the mixture is stirred for another 10 min before quenching with H2O and 5 N NaOH. After which, EtOAc is added and the organic layer is collected and washed with brine and dried over Na2SO4. Removal of the solvent provided the crude amine, which is used directly in the next step. MS (ESI): 301 (M+1)+1.

Workup

  1. additionAfter addition
  2. custombefore quenching with H2O and 5 N NaOH
  3. additionAfter which, EtOAc is added
  4. customthe organic layer is collected
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-b7d6456936b845089986302fe748cc13
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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