Aluminium lithium hydride → HCID 178420861, compound

HRID 1909000Notes

Reaction equation

HRID 1909000 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=O)=[CH:9][C:4]=2[N:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:12]1([CH2:10][C:8]2[CH:7]=[CH:6][C:5]3[NH:1][CH:2]=[N:3][C:4]=3[CH:9]=2)[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178519372HCID 178519372, compound

Product 1

HCID 178420861HCID 178420861, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (1H-benzoimidazol-5-yl)-morpholin-4-yl-methanone (1 g, 4.32 mmol) in THF (60 mL) at 0° C. was added LiAlH4 (2M in THF; 4.32 mL, 8.65 mmol) dropwise. The mixture was stirred 0° C. for 2 hours then warmed to room temperature for 2 hours. The mixture was cooled again to 0° C. and then quenched by addition of H2O (0.328 mL), followed by 15% aqueous NaOH solution (0.328 mL) and finally H2O (3×0.328 mL). The mixture was stirred for 1 hour and left to stand overnight. The mixture was diluted with THF, filtered, concentrated in vacuo and purified by SiO2 chromatography to give 5-morpholin-4-ylmethyl-1H-benzoimidazole (838 mg). Step 3 was performed by repeating procedures described for Example 1 then gave the title compound as a mixture of two regioisomers.

Workup

  1. temperaturethen warmed to room temperature for 2 hours
  2. temperatureThe mixture was cooled again to 0° C.
  3. customquenched by addition of H2O (0.328 mL)
  4. stirringThe mixture was stirred for 1 hour
  5. waitleft
  6. waitto stand overnight
  7. additionThe mixture was diluted with THF
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. custompurified by SiO2 chromatography

Sources & evidence

ORD record
ord-d0bed6c8da954b4ea08a02ebe79c2dd5
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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