Hydrochloric Acid → HCID 45261661, compound

HRID 566566Notes

Reaction equation

HRID 566566 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14]/[CH:15]=[C:16](/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])\[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:33]CCl>C(O)C.CC(C)=O>[ClH:33].[CH3:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[C:16](/[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:15]/[O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 10502731HCID 10502731, compound

Product 1

HCID 45261661HCID 45261661, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

E-(R)-1-(2-((2-(2-Methylphenyl)-2-phenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (1.1 g, 0.0028 mol, prepared similarly to the method described in Example 50) was dissolved in ethanol (5 ml) and 12 N sodium hydroxide solution (0.7 ml) was introduced. After stirring the solution at room temperature for 2 h, 37% hydrochloric acid solution (ca. 1.0 ml) was added (with cooling) followed by dichloromethane (300 ml) and the mixture was dried (Na2SO4). Filtration and evaporation of the filtrate gave a residue, which was co-evaporated with acetone. The solid product was triturated with ethyl acetate, collected by filtration and dried in vacuo to provide the title compound (0.70 g, 62%).

Workup

  1. temperature(with cooling)
  2. dry with materialthe mixture was dried (Na2SO4)
  3. filtrationFiltration and evaporation of the filtrate
  4. customgave a residue, which
  5. customThe solid product was triturated with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-f2f19d7e8ac74bc0911fbfe3078eda65
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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