Hydrochloric Acid → HCID 45265040, compound

HRID 1460651Notes

Reaction equation

HRID 1460651 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-4d75e109a7904245be4445587aa66c8b
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

Loading…