Hydrogen chloride-ethyl acetate → HCID 22678626, compound

HRID 1837775Notes

Reaction equation

HRID 1837775 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2C)[CH2:12][CH2:11]1.[C:25]([O:28]CC)(=[O:27])C.Cl>C(O)C>[O:2]=[C:3]1[CH:8]=[CH:7][NH:6][CH:5]=[C:4]1[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]3[O:27][CH2:25][O:28][C:19]=23)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22678433HCID 22678433, compound

Product 1

HCID 22678626HCID 22678626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

259 mg of 1-[(4-methoxy-3-pyridinyl)methyl]-4-[2-(2-methylphenyl)ethyl]piperidine was dissolved in 5 ml of ethanol. To the mixture was added 1.91 ml of a hydrogen chloride-ethyl acetate solution, followed by heating under reflux overnight. The solvent was evaporated, and to the residue was added a 2N hydrochloric acid (15 ml), followed by heating under reflux for further 7 hours. A sodium carbonate aqueous solution was added to the reaction solution, and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The crude product was purified by NH-silica gel column chromatography (n-hexane:ethyl acetate=2:1), to give 42 mg of the title compound as a white powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. customThe solvent was evaporated
  4. additionto the residue was added a 2N hydrochloric acid (15 ml)
  5. temperatureby heating
  6. temperatureunder reflux for further 7 hours
  7. additionA sodium carbonate aqueous solution was added to the reaction solution
  8. extractionthe mixture was extracted with chloroform
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated
  11. customThe crude product was purified by NH-silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a8d5b135b26a49fbad69a9a7b060b6c8
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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