Hydrochloric Acid → HCID 70228308, compound

HRID 1460666Notes

Reaction equation

HRID 1460666 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 12N 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-28372267969a424197483e9e34fb0920
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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