Hydrochloric Acid → HCID 59365378, compound

HRID 218046Notes

Reaction equation

HRID 218046 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([NH:28]C(=O)C)[CH:23]=4)[CH2:18][CH2:17]3)[C:11]3[CH:32]=[CH:33][CH:34]=[CH:35][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=4)[CH2:20][CH2:21]3)[C:11]3[CH:32]=[CH:33][CH:34]=[CH:35][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25058425HCID 25058425, compound

Product 1

HCID 59365378HCID 59365378, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g (3.08 mmol) of 2-(4-chlorophenyl)-1-{3-[4-(3-acetylaminophenyl)piperidin-1-yl]propyl}-1H-benzimidazole obtained in Example 4 was dissolved in 30 ml of methanol, and 10 ml of 5N—HCl aqueous solution was added to the resulting solution, followed by mixing the solution at 50° C. for 3 hours. The resulting solution was concentrated under a reduced pressure and 60 ml of water was added thereto. Then, pH of the solution was adjusted to 8 or more. The reaction mixture was extracted with ethylacetate (80 ml×2) being washed with water and a sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was removed under a reduced pressure, and the resulting residue was refined by silica gel column chromatography (n-hexane/ethylacetate=1/3) to obtain 1.19 g (yield 87%) of the title compound.

Workup

  1. additionby mixing the solution at 50° C. for 3 hours
  2. concentrationThe resulting solution was concentrated under a reduced pressure and 60 ml of water
  3. additionwas added
  4. extractionThe reaction mixture was extracted with ethylacetate (80 ml×2)
  5. washbeing washed with water
  6. dry with materiala sodium hydroxide solution, and then the combined organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-f45307c1e6524c2e97e4c0c1cf42d3fc
Source dataset
uspto-grants-2012_06
Patent number
US08198307B2

Reaction notes

Loading…