1,4'-Bipiperidine → HCID 71182996, compound

HRID 245227Notes

Reaction equation

HRID 245227 reaction equation
Br[CH2:2][C:3]1[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=[C:8]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:7]=2.[N:31]1([CH:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C(#N)C>[N:31]1([CH:37]2[CH2:42][CH2:41][N:40]([CH2:2][C:3]3[C:4]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)=[N:5][C:6]4[C:11]([C:12]=3[C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=[C:8]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:7]=4)[CH2:39][CH2:38]2)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 786071,4'-BipiperidineHCID 67383469HCID 67383469, compound

Product 1

HCID 71182996HCID 71182996, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of methyl 3-(bromomethyl)-7-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (0.713 g, 1.42 mmol) and 1,4′-bipiperidine (0.311 g, 1.846 mmol) in acetonitrile (25 mL) was stirred at room temperature for 3 h. The solvent was removed under reduced pressure. The residue was diluted with saturated aqueous NaHCO3, and the mixture was extracted with methylene chloride (three time). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-10% MeOH with 0.1% NH3/CH2Cl2) to give methyl 3-(1,4′-bipiperidin-1′-ylmethyl)-7-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (0.730 g, 87% yield). MS (m/z) 590.2 (M+H+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with saturated aqueous NaHCO3
  3. extractionthe mixture was extracted with methylene chloride (three time)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via column chromatography (ISCO, 0-10% MeOH with 0.1% NH3/CH2Cl2)

Sources & evidence

ORD record
ord-d7e476f0eb0e4d6895516a4b934bdf04
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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