Potassium Carbonate → HCID 21188559, compound

HRID 1384019Notes

Reaction equation

HRID 1384019 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([O:13][C:14]2[C:22]3[N:21]=[C:20]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[N:19]([CH2:32][CH2:33][CH2:34][CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[C:47]1([CH2:53][CH2:54][CH2:55]Br)[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C)C=O>[CH:8]1([O:13][C:14]2[C:22]3[N:21]=[C:20]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[N:19]([CH2:32][CH2:33][CH2:34][CH:35]4[CH2:40][CH2:39][N:38]([CH2:55][CH2:54][CH2:53][C:47]5[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=5)[CH2:37][CH2:36]4)[C:18]=3[CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 21188722HCID 21188722, compound

Product 1

HCID 21188559HCID 21188559, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-cyclopentoxy-2-[(4-chlorophenoxy)methyl]-1-[3-(piperidin-4-yl)propyl]benzimidazole trifluoroacetate (0.29 mmol, 1 eq) in anhydrous N,N-dimethylformamide (2 ml) was treated with potassium carbonate (120 mg, 0.87 mmol, 3 eq) and 3-phenylpropyl bromide (87 mg, 0.43 mmol, 1.5 eq). The resulting mixture was stirred at 80° C. for six hours. The reaction was quenched by the addition of water (5 ml). The aqueous fraction was extracted with ethyl acetate (3×10 ml). The organic fractions were combined, washed with water (3×10 ml), and brine (1×10 ml), and then dried over sodium sulfate. The solvents were removed in vacuo. The residue was further purified by column chromatography to yield the title product as a white crystalline solid.

Workup

  1. customThe reaction was quenched by the addition of water (5 ml)
  2. extractionThe aqueous fraction was extracted with ethyl acetate (3×10 ml)
  3. washwashed with water (3×10 ml), and brine (1×10 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customThe residue was further purified by column chromatography

Sources & evidence

ORD record
ord-4d12d279a2334cc79ddd6588ec800361
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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