Hydrochloric Acid → HCID 45265040, compound

HRID 249436Notes

Reaction equation

HRID 249436 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14]/[CH:15]=[C:16](\[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>C(O)C>[ClH:29].[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[C:16](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:15]\[O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 14798Sodium HydroxideHCID 10527539HCID 10527539, compound

Product 1

HCID 45265040HCID 45265040, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

E or Z-(R)-1-[2-[[2-(2-Chlorophenyl)-2-phenylethenyl]oxy]-ethyl]-3-piperidine carboxylic acid ethyl ester (1.0 g, 0.0024 mol) (prepared as described in Method A) was dissolved in ethanol (10 ml) and 10N sodium hydroxide solution (2.42 ml) was introduced. After stirring the solution at room temperature for 5 h, water (100 ml) was added and the mixture was neutralized with 2N hydrochloric acid solution. Evaporation of ethanol under reduced pressure gave an aqueous solution, which was acidified to pH 0.5 with 2N hydrochloric acid solution and extracted with dichloromethane (4 × 100 ml). The combined extracts were dried (Na2SO4) and evaporated to an oil, which was dissolved in a trace of methanol. Toluene (20 ml) was introduced, and the product solution was heated on a steam bath. On cooling the title compound (0.64 g, 62%), a white crystalline solid, was collected and dried in vacuo. M.p. softens at 170°, melts at 198°.

Workup

  1. customEvaporation of ethanol under reduced pressure
  2. customgave an aqueous solution, which
  3. extractionextracted with dichloromethane (4 × 100 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated to an oil, which
  6. dissolutionwas dissolved in a trace of methanol
  7. additionToluene (20 ml) was introduced
  8. temperaturethe product solution was heated on a steam bath
  9. temperatureOn cooling the title compound (0.64 g, 62%)
  10. customa white crystalline solid, was collected
  11. customdried in vacuo
  12. customsoftens at 170°

Sources & evidence

ORD record
ord-579a9f0144e6479f8830d8d2ebfa6fc1
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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