Lithium hydride → HCID 69154773, compound

HRID 1417203Notes

Reaction equation

HRID 1417203 reaction equation
[Al].[H-].[Li+].[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:39])([CH3:38])[C:33](OCC)=[O:34])=[CH:28][CH:27]=2)[CH2:20][CH2:19]1)[CH3:5].[H-]>C1COCC1.O>[CH2:4]([O:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=[C:10]1[CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:32]([CH3:38])([CH3:39])[CH2:33][OH:34])=[CH:30][CH:31]=2)[CH2:20][CH2:19]1)[CH3:5]

Participants

7

Reactant 4

HCID 62714Lithium hydrideHCID 166653HydrideHCID 5359268AluminumHCID 66869688Ethyl 2-[4-(2-(4-(1-(2-ethoxyethyl)benzimidazole-2-yl)piperidine-1-yl)ethyl)phenyl]-2-methylpropanoate

Product 1

HCID 69154773HCID 69154773, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 g of aluminium and lithium hydride was dissolved in 30 ml of THF and 3 g of ethyl 2-[4-(2-(4-(1-(2-ethoxyethyl)benzimidazole-2-yl)piperidine-1-yl)ethyl)phenyl]-2-methylpropanoate were added dropwise thereto. This was stirred for four hours at room temperature and some milliliters of water were added to eliminate excess hydride. The solution was filtered and the filtrate was washed with a saturated sodium chloride solution. This was dried and concentrated. The residue was redissolved in chloroform and washed with water, dried and concentrated. The residue was purified by flash-chromatography using a hexane/ether/isopropyl-amine mixture (2/7.5/0.5) as an eluent, to yield 1.5 g of 1-(2-ethoxyethyl)-2-[1-(2-(4-(1,1-dimethyl-2-hydroxyethyl)phenyl)ethyl)piperidine-4-yl]-1H-benzimidazole.

Workup

  1. filtrationThe solution was filtered
  2. washthe filtrate was washed with a saturated sodium chloride solution
  3. customThis was dried
  4. concentrationconcentrated
  5. dissolutionThe residue was redissolved in chloroform
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-2ee53132c2cb46e0931b9022faefd13c
Source dataset
uspto-grants-1999_03
Patent number
US05877187

Reaction notes

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