Potassium Carbonate → HCID 21188524, compound

HRID 1384017Notes

Reaction equation

HRID 1384017 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[C:18]2[N:17]=[C:16]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:15]([CH2:28][CH2:29][CH2:30][CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:14]=2[CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[C:43]1([CH2:49][CH2:50][CH2:51]Br)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C)C=O>[CH3:8][O:9][C:10]1[C:18]2[N:17]=[C:16]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[N:15]([CH2:28][CH2:29][CH2:30][CH:31]3[CH2:32][CH2:33][N:34]([CH2:51][CH2:50][CH2:49][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH2:35][CH2:36]3)[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 21188535HCID 21188535, compound

Product 1

HCID 21188524HCID 21188524, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-methoxy-2-[(4-chlorophenoxy)methyl]-1-[3-(piperidin-4-yl)propyl]benzimidazole trifluoroacetate (177 mg, 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-aa915b8018f240e5bc34799951a89546
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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