Aluminium lithium hydride → HCID 68671644, compound

HRID 2047377Notes

Reaction equation

HRID 2047377 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:12]=[C:13]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([CH:25]3[CH2:30][O:29][CH2:28][CH2:27][N:26]3[CH3:31])=O)[CH2:19][CH2:18]2)[CH:14]=[CH:15][CH:16]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH:25]3[CH2:30][O:29][CH2:28][CH2:27][N:26]3[CH3:31])[CH2:21][CH2:22]2)[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 68671138HCID 68671138, compound

Product 1

HCID 68671644HCID 68671644, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-[3-(1-Methyl-1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-(4-methyl-morpholin-3-yl)-methanone (0.06 g, 0.16 mmol) in dry THF (2 mL) at room temperature under a nitrogen atmosphere was added lithium aluminium hydride (LiAlH4) (0.02 g, 0.47 mmol). The reaction was heated at reflux for 2 h and other LiAlH4 (0.01 g, 0.24 mmol). After 30 min the solution was cooled to room temperature, quenched with 10% NaOH (3 mL) and then extracted with dichloromethane (3×3 mL) The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude was then purified by Preparative HPLC to obtain 0.03 g (41%) of the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. customquenched with 10% NaOH (3 mL)
  4. extractionextracted with dichloromethane (3×3 mL) The combined organic layers
  5. dry with materialwere dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was then purified by Preparative HPLC

Sources & evidence

ORD record
ord-0285b308ca144c02b7ddeba324a65153
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Reaction notes

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