Hydrochloric Acid → HCID 70230442, compound

HRID 249450Notes

Reaction equation

HRID 249450 reaction equation
Cl.FC1[CH:4]=[C:5]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25](F)[CH:24]=2)=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl.[Cl:33][CH2:34][Cl:35].[CH2:36](O)C>>[ClH:33].[Cl:35][C:34]1[CH:4]=[C:5]([C:9]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[CH3:36])=[CH:10][O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 45264923HCID 45264923, compound

Product 1

HCID 70230442HCID 70230442, compoundYield 55%

Procedure

1-[2-[[2-(3-Chlorophenyl)-2-(2-methylphenyl)ethenyl]oxy]-ethyl]-1,2, 5,6-tetrahydro-3-pyridine carboxylic methyl ester (0.60 g, 0.0014 mol) (prepared as described in Method D) was dissolved in ethanol (5 ml) and 12 N sodium hydroxide solution (0.35 ml) was introduced. After stirring the solution at room temperature for 3 h, 37% hydrochloric acid solution was added, until the pH was measured as ca. 1. Dichloromethane (200 ml) was introduced, and the mixture was dried (Na2SO4), filtered and evaporated to a residue, which was co-evaporated twice with acetone. The residue was recrystallized from acetone/ethyl acetate to give the title compound (0.33 g, 55%) as white crystals, m.p. 168°-170° HPLC retention times 16.12 and 18.42 for the geometric isomers (gradient elution, water/20-80% acetonitrile, both phases containing 0.1% TFA).

Workup

  1. dry with materialthe mixture was dried (Na2SO4)
  2. filtrationfiltered
  3. customevaporated to a residue, which
  4. customThe residue was recrystallized from acetone/ethyl acetate

Sources & evidence

ORD record
ord-159d064872a844be9fca00c7f2b51bb0
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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