Sodium Bicarbonate → HCID 22678688, compound

HRID 1837768Notes

Reaction equation

HRID 1837768 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:32]([O:35]CC)(=[O:34])C.Cl.[C:39](=[O:42])([OH:41])[O-].[Na+]>C(O)C>[C:32]([OH:35])(=[O:34])[C:39]([OH:41])=[O:42].[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 22678329HCID 22678329, compound

Product 1

HCID 22678688HCID 22678688, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (4 ml) was dissolved 226 mg of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-[2-(cyclohexylmethyloxy)phenyl]ethyl]piperidine. To the mixture was added 1 ml of a 4N-hydrogen chloride-ethyl acetate solution, followed by heating under reflux for 1.5 hours. An aqueous sodium bicarbonate was added to the reaction solution, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting oil was dissolved in ethanol, 49 mg of oxalic acid and ethyl acetate were added thereto, and then the resulting precipitates were collected by filtration, to give 229 mg of the title compound as a white powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe resulting oil was dissolved in ethanol
  7. addition49 mg of oxalic acid and ethyl acetate were added
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e8135d825118440f966b56aa04a2db31
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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