Potassium Carbonate → HCID 21188744, compound

HRID 1384023Notes

Reaction equation

HRID 1384023 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)[N:21]([CH2:34][CH2:35][CH2:36][CH:37]4[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].[C:49]1([CH2:55][CH2:56][CH2:57]Br)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>CN(C)C=O>[CH:8]1([CH2:14][O:15][C:16]2[C:24]3[N:23]=[C:22]([CH2:25][O:26][C:27]4[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=4)[N:21]([CH2:34][CH2:35][CH2:36][CH:37]4[CH2:38][CH2:39][N:40]([CH2:57][CH2:56][CH2:55][C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)[CH2:41][CH2:42]4)[C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 21188748HCID 21188748, compound

Product 1

HCID 21188744HCID 21188744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-(cyclohexylmethoxy)-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-58bfc303416f46a0b96a3a0b26f6206c
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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