Hydrochloric Acid → HCID 70228308, compound

HRID 566573Notes

Reaction equation

HRID 566573 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]=[C:25]([O:29][CH3:30])[CH:24]=2)[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+].Cl.[Cl:34]CCl>C(O)C.O>[ClH:34].[CH3:30][O:29][C:25]1[CH:24]=[C:23]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:14][O:13][CH2:12][CH2:11][N:7]2[CH2:8][CH2:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH2:6]2)[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54342470HCID 54342470, compound

Product 1

HCID 70228308HCID 70228308, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(2-((2-(3-Methoxyphenyl)-2-(2-methylphenyl)ethenyl)oxy)ethyl)-1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester (1.15 g, 0.0027 mol, prepared similarly to the method described in Example 70) was dissolved in ethanol (15 ml) and 12 N sodium hydroxide solution (0.5 ml) was introduced. After stirring the solution at room temperature for 4 h, ice (30 g) was added, and pH of the reaction mixture was adjusted to ca. 7 with 37% hydrochloric acid solution. Dichloromethane (200 ml) was added, and the pH was further adjusted to ca. 1 with 37% hydrochloric acid solution. Water was added until the solid material was dissolved, and the dichloromethane phase was dried (Na2SO4) and evaporated to an oil, which was co-evaporated three times with acetone. The residue was triturated with diethyl ether to give the title compound (0.60 g, 52%).

Workup

  1. dissolutionwas dissolved
  2. dry with materialthe dichloromethane phase was dried (Na2SO4)
  3. customevaporated to an oil, which
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2200752693ce48e28339ce46ab8fad38
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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