Hydrochloric Acid → HCID 70228233, compound

HRID 1460672Notes

Reaction equation

HRID 1460672 reaction equation
C(C(C(C(O)=O)O)O)(O)=O.C([O:13][C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:22][CH2:23][CH2:24][O:25][CH:26]=[C:27]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[CH2:17]1)=[O:15])C.[OH-].[Na+].[ClH:44]>C(O)C>[ClH:44].[F:41][C:38]1[CH:37]=[CH:36][C:35]([C:27]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)=[CH:26][O:25][CH2:24][CH2:23][CH2:22][N:18]2[CH2:19][CH2:20][CH2:21][C@@H:16]([C:14]([OH:15])=[O:13])[CH2:17]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70230542HCID 70230542, compound

Product 1

HCID 70228233HCID 70228233, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-[3-[[2,2-bis(4-Fluorophenyl)ethenyl]oxy]propyl]-3-piperidine carboxylic acid ethyl ester tartrate (3.8 g, 0.0065 mol) (prepared as described in Method D) was dissolved in ethanol (25 ml) and 12N sodium hydroxide solution (2.2 ml) was introduced at 5°. After stirring the solution at room temperature for 4.8 h, the pH of the reaction mixture was adjusted to ca. 7 with 4N hydrochloric acid solution, and the mixture was evaporated to a residue in vacuo. Water (25 ml) was added, and the mixture was extracted with dichloromethane (3×50 ml). The combined extracts were dried (MgSO4) and evaporated to a foam, which was dissolved in toluene (1.5 ml) and warmed to 40°. Methanol (0.27 ml) was introduced followed by chlorotrimethylsilane (0.83 ml). The product precipitated slowly, and after the suspension had been allowed to stand for 18 h at room temperature it was collected by filtration. The title compound (2.9 g, quant.) was obtained as white crystals, m.p. 177°-180° (after drying in vacuo). HPLC retention time 12.55 (gradient elution, water/35-50% acetonitrile, aqueous phase containing 0.1M ammonium sulphate solution).

Workup

  1. customthe mixture was evaporated to a residue in vacuo
  2. additionWater (25 ml) was added
  3. extractionthe mixture was extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated to a foam, which
  6. dissolutionwas dissolved in toluene (1.5 ml)
  7. temperaturewarmed to 40°
  8. additionMethanol (0.27 ml) was introduced
  9. customThe product precipitated slowly
  10. waitto stand for 18 h at room temperature
  11. filtrationit was collected by filtration

Sources & evidence

ORD record
ord-48a3a99289a14f3cacfee8e62aa09bdf
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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