Hydrochloric Acid → HCID 45261615, compound

HRID 566565Notes

Reaction equation

HRID 566565 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 10765047HCID 10765047, compound

Product 1

HCID 45261615HCID 45261615, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Z-(R)-1-(2-((2-(2-Methylphenyl)-2-phenylethenyl)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester (2.0 g, 0.0051 mol, prepared similarly to the method described in Example 50) was dissolved in ethanol (8 ml) and 12 N sodium hydroxide solution (1.3 ml) was introduced. After stirring the solution at room temperature for 2 h, 37% hydrochloric acid (ca. 1.8 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 filtratiion and dried in vacuo to give the title compound (0.70 g, 34%).

Workup

  1. temperaturewith 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. customcollected by filtratiion
  7. customdried in vacuo

Sources & evidence

ORD record
ord-282986b367b34fb093c77abfee56fce6
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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