Hydrogen chloride-ethyl acetate → HCID 22678617, compound

HRID 1837747Notes

Reaction equation

HRID 1837747 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([C:19]3[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:18])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(OC(=O)C)C.Cl>C(#N)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][C:17]([C:19]3[C:20]([Cl:25])=[N:21][CH:22]=[CH:23][CH:24]=3)=[O:18])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22678642HCID 22678642, compound

Product 1

HCID 22678617HCID 22678617, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In acetonitrile (4 ml) were dissolved 100 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(2-chloro-3-pyridyl)-2-oxoethyl)piperidine obtained in Example 62 and 0.35 ml of a 4 M hydrogen chloride ethyl acetate solution, followed by heating under reflux for 1 hour. The solvent was evaporated, and then the residue was dissolved in ethyl acetate and a 1N sodium hydroxide aqueous solution. The organic layer was separated, washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was recrystallized from ethanol, to give 46 mg of the title compound as colorless crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-aed0d5ccde964bc89b9c88f4945e178e
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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