Ethanol → HCID 23366918, compound

HRID 1079385Notes

Reaction equation

HRID 1079385 reaction equation
C([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=O)C.[C:22](=[O:25])([O-:24])[O-].[K+].[K+].C([OH:30])C>O.Cl>[C:11]([OH:30])(=[O:10])/[CH:12]=[CH:13]/[C:22]([OH:24])=[O:25].[N:17]1([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH:7]3[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]3)=[CH:16][CH:15]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 23366934HCID 23366934, compound

Product 1

HCID 23366918HCID 23366918, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-Acetyl-4-(4-pyrrolidinopheyloxy)piperidine (1.5 g) obtained in Example 1 was dissolved in a mixed solvent of ethanol (5 ml), water (5 ml) and conc. hydrochloric acid (5 ml), followed by heating with stirring at 100° C. for 15 hours. The solution was made basic with potassium carbonate and then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residual oily compound (1.22 g) was dissolved in methanol (30 ml). After fumaric acid (0.52 g) was dissolved in the solution, the solvent was distilled off to leave a solid which was recrystallized from ethanol to obtain colorless crystals (1.4 g), m.p. 199°-201° C.

Workup

  1. temperatureby heating
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. dissolutionThe residual oily compound (1.22 g) was dissolved in methanol (30 ml)
  6. dissolutionAfter fumaric acid (0.52 g) was dissolved in the solution
  7. distillationthe solvent was distilled off
  8. customto leave a solid which
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4d7831319aca41d4a27b40208448a49f
Source dataset
uspto-grants-1996_12
Patent number
US05580883

Reaction notes

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