Potassium hydride → diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioate

HRID 1648288Notes

Reaction equation

HRID 1648288 reaction equation
[H-].[K+].[CH2:3]([N:6]([CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH3:9])[CH2:4][CH3:5].Br[CH2:22][C:23]1[C:31]2[N:30]=[CH:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:27]=2[CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH3:37][C:35]([CH3:38])([O:34][C:32]([N:28]1[C:27]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:22][C:10]([N:6]([CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][CH3:5])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:31]=2[N:30]=[CH:29]1)=[O:33])[CH3:36]

Participants

5

Reactant 3

HCID 82127Potassium hydrideHCID 15744964tert-Butyl 4-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylateHCID 15744966Diethyl (dipropylamino)propanedioate

Product 1

HCID 15744967diethyl {((1,1-dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropylamino)-propanedioateYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium hydride (3.3 g of 40% oil suspension, washed with ether to remove oil, 0.03 mol) was added to a stirred solution of diethyl (dipropylamino)-malonate (10.2 g, 0.039 mol) in dry THF (100 mL). After 5 minutes, t-butyl 4-(bromomethyl) -1H-benzimidazole-1-carboxylate (6.22 g, 0.02 mol) was added and the solution was refluxed for 6 hours. The solvent was removed under reduced pressure and the residual oil was partitioned between ethyl acetate and water. After evaporation of the ethyl acetate, the crude product was chromatographed on silica gel using ethyl acetate:hexane as the eluant to give 7.9 g of diethyl {((1,1 -dimethylethoxycarbonyl)-1H-benzimidazole-4-yl)methyl}(dipropyl amino)-propanedioate as an oil.

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residual oil was partitioned between ethyl acetate and water
  4. customAfter evaporation of the ethyl acetate
  5. customthe crude product was chromatographed on silica gel

Sources & evidence

ORD record
ord-02c10acca5c44d4182e4e0f418745082
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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