Hydrochloric Acid → HCID 10788634, compound

HRID 249443Notes

Reaction equation

HRID 249443 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[S:24][CH:25]=[CH:26][C:27]=2[CH3:28])[C:17]2[S:18][CH:19]=[CH:20][C:21]=2[CH3:22])[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH3:22][C:21]1[CH:20]=[CH:19][S:18][C:17]=1[C:16]([C:23]1[S:24][CH:25]=[CH:26][C:27]=1[CH3:28])=[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10598185HCID 10598185, compound

Product 1

HCID 10788634HCID 10788634, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-1-[2-[[2,2-bis(3-Methyl-2-thienyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic ethyl ester (420 mg, 1 mmol) (example 11) was dissolved in ethanol (20 ml) and 10 N sodium hydroxide solution (1.00 ml) was introduced. After 3 h at room temperature the pH of the solution was adjusted to 9 with 2 N hydrochloric acid. The ethanol was removed by evaporation and the pH of the solution was adjusted to 2.5. Extraction with dichloromethane (4 × 15 ml), drying of the combined extracts (MgSO4) (charcoal decolourisation) and evaporation of the filtrate provided a residue, which was recrystallized from water. This provided the title compound (0.34 g, 84%) as a cream solid, m.p. 55°-70° C. TLC: rf 0.37 (SiO2, CH2Cl2 /MeOH 1/1).

Workup

  1. customThe ethanol was removed by evaporation
  2. extractionExtraction with dichloromethane (4 × 15 ml)
  3. dry with materialdrying of the combined extracts (MgSO4) (charcoal decolourisation) and evaporation of the filtrate
  4. customprovided a residue, which
  5. customwas recrystallized from water

Sources & evidence

ORD record
ord-ea904f362e65434388af75d2a7966e8d
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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