Hydrochloric Acid → HCID 45265023, compound

HRID 249444Notes

Reaction equation

HRID 249444 reaction equation
C[O:2][C:3]([C:5]1[CH2:6][N:7]([CH2:11][CH2:12][O:13][CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH2:8][CH2:9][CH:10]=1)=[O:4].[OH-].[Na+].O.[ClH:33]>C(O)C>[ClH:33].[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])=[CH:14][O:13][CH2:12][CH2:11][N:7]1[CH2:8][CH2:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH2:6]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 53881273HCID 53881273, compound

Product 1

HCID 45265023HCID 45265023, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2-[[2,2-bis(2-Methylphenyl)ethenyl]oxy]ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester (0.70 g, 0.0018 mol) (prepared as described in Method B) was dissolved in ethanol (30 ml) and 10 N sodium hydroxide solution (1.79 ml) was introduced. The reaction mixture was stirred at room temperature for 2.5 h and water (100 ml) was added, followed by 2 N hydrochloric acid solution to pH 10. Ethanol was removed by evaporation under reduced pressure, and the aqueous solution was washed with ethyl acetate (20 ml). The aqueous phase was separated, acidified to pH 2 with 2 N hydrochloric acid solution, and extracted with dichloromethane (4 × 50 ml). The combined extracts were dried (MgSO4) and the residue was crystallized from propanol/toluene to give the title compound (0.53 g, 76%), m.p. 195°-198°.

Workup

  1. customEthanol was removed by evaporation under reduced pressure
  2. washthe aqueous solution was washed with ethyl acetate (20 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane (4 × 50 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe residue was crystallized from propanol/toluene

Sources & evidence

ORD record
ord-0da3102441bc4c38bde75d64ec9890c1
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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