Hydrochloric Acid → HCID 45265023, compound

HRID 566570Notes

Reaction equation

HRID 566570 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-tetrahydro-3-pyridinecarboxylic acid methyl ester (0.70 g, 0.0018 mol, prepared similarly to the method described in Example 65) 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 was dried (MgSO4) and the residue was crystallized from propanol/toluene to give the title compound (0.53 g, 76%).

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 was dried (MgSO4)
  6. customthe residue was crystallized from propanol/toluene

Sources & evidence

ORD record
ord-7dfbc856c737457fa518168d2dfd93cc
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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