Hydrochloric Acid → HCID 45261650, compound

HRID 566567Notes

Reaction equation

HRID 566567 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH2:14][O:15][CH:16]=[C:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:33]CCl>C(O)C.CC(C)=O>[ClH:33].[C:24]1([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][O:15][CH2:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54493495HCID 54493495, compound

Product 1

HCID 45261650HCID 45261650, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

(R)-1-(3-((2,2-Diphenylethenyl)oxy)propyl)-3-piperidinecarboxylic acid ethyl ester (0.60 g, 0.0015 mol, prepared similarly to the method described in Example 50) was dissolved in ethanol (5 ml) and 12 N sodium hydroxide solution (0.4 ml) was introduced. After stirring the solution at room temperature for 2 h, 37% hydrochloric acid (ca. 0.52 ml) was added with cooling followed by dichloromethane (250 ml). The mixture was dried (Na2SO4). Filtration and evaporation 15 of the filtrate gave a residue, which was co-evaporated with acetone. The solid product was triturated with acetone, collected by filtration and dried in vacuo to give the title compound (0.30 g, 50%).

Workup

  1. temperaturewith cooling
  2. dry with materialThe mixture was dried (Na2SO4)
  3. filtrationFiltration and evaporation 15 of the filtrate
  4. customgave a residue, which
  5. customThe solid product was triturated with acetone
  6. filtrationcollected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e8f7c162378c41ddb5991d021f851c3e
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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