Hydrochloric Acid → HCID 70228308, compound

HRID 249449Notes

Reaction equation

HRID 249449 reaction equation
Cl.F[C:3]1[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.[CH2:36]([OH:38])C>O>[ClH:33].[CH3:36][O:38][C:3]1[CH:4]=[C:5]([C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:34])=[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

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 45264923HCID 45264923, compound

Product 1

HCID 70228308HCID 70228308, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[2-[[2-(3-Methoxyphenyl)-2-(2-methylphenyl)ethenyl]oxy]-ethyl]-1, 2,5,6-tetrahydro-3-pyridine carboxylic acid methyl ester (1.15 g, 0.0027 mol) (prepared as described in Method D) 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 the 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%), which gave HPLC retention times of 17.1 and 17.6 min. for the geometric isomers (gradient elution, water/20-80% acetonitrile, both containing 0.1% TFA).

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-c767c35253d34105ade0b6cd8bbc4b23
Source dataset
uspto-grants-1993_05
Patent number
US05214057

Reaction notes

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