Potassium Carbonate → HCID 21188808, compound

HRID 1384021Notes

Reaction equation

HRID 1384021 reaction equation
FC(F)(F)C(O)=O.[CH:8]([O:11][C:12]1[C:20]2[N:19]=[C:18]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[N:17]([CH2:30][CH2:31][CH2:32][CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].[C:45]1([CH2:51][CH2:52][CH2:53]Br)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C)C=O>[CH:8]([O:11][C:12]1[C:20]2[N:19]=[C:18]([CH2:21][O:22][C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[N:17]([CH2:30][CH2:31][CH2:32][CH:33]3[CH2:34][CH2:35][N:36]([CH2:53][CH2:52][CH2:51][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:37][CH2:38]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 21188520HCID 21188520, compound

Product 1

HCID 21188808HCID 21188808, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4-isopropoxy-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-5dd5a86233ed4447a205cd743fb5347f
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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