Ethanol → HCID 15744969, compound

HRID 327446Notes

Reaction equation

HRID 327446 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]([CH2:27][CH2:28][CH3:29])[CH:11]([CH2:17][C:18]1[C:26]2[N:25]=[CH:24][NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1)[C:12](OCC)=[O:13])[CH2:8][CH3:9].C(Cl)(Cl)Cl.C(O)C>C1COCC1.CO>[CH2:27]([N:10]([CH2:7][CH2:8][CH3:9])[CH:11]([CH2:17][C:18]1[C:26]2[N:25]=[CH:24][NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1)[CH2:12][OH:13])[CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 15744968132873-78-0HCID 21226445Aluminium lithium hydride

Product 1

HCID 15744969HCID 15744969, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (250 mg, 6.6 mmol) was added at 0° C. to a stirred solution of ethyl α-(dipropylamino)-1H-benzimidazole-4-propanoate (1.5 g, 4.7 mmol) in dry THF (50 mL), and the solution was allowed to warm to room temperature. TLC in 10% methanol:chloroform showed that the reaction was complete in 15 minutes. Ethanol (5 mL) was added and the solvents were removed under reduced pressure. The residue was partitioned between ethyl acetate and water. Evaporation of the ethyl acetate gave 1.3 g of β-(dipropylamino)-1H-benzimidazole-4-propanol which was used without further purification.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customEvaporation of the ethyl acetate

Sources & evidence

ORD record
ord-4b7881355bb6451d99fa467ec2360dfd
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

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