Hydrochloric Acid → HCID 45265040, compound

HRID 1460652Notes

Reaction equation

HRID 1460652 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[Cl:29])/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].O.Cl>C(O)C>[ClH:29].[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1/[C:16](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 14798Sodium HydroxideHCID 10527539HCID 10527539, compound

Product 1

HCID 45265040HCID 45265040, compoundYield 114.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

E or Z-(R)-1-[2-[[2-(2-Chlorophenyl)-2-phenylethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (1.0 g, 0.0024 mol) (opposite geometric isomer of example 6) was dissolved in ethanol (20 ml) and 10N sodium hydroxide solution (2.42 ml) was introduced. After stirring the reaction mixture at room temperature for 16 h, water (100 ml) was added and the mixture was neutralized with 2N hydrochloric acid solution. Evaporation of ethanol under reduced pressure gave an aqueous solution, which was acidified to pH 1 with 2N hydrochloric acid and extracted with dichloromethane (4×100 ml). The combined extracts were dried (Na2SO4) and evaporated to a solid, which was recrystallized from methanol/toluene to give the title compound (0.58 g, 56%) as white crystals (after drying in vacuo), m.p 227-8°.

Workup

  1. customEvaporation of ethanol under reduced pressure
  2. customgave an aqueous solution, which
  3. extractionextracted with dichloromethane (4×100 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customevaporated to a solid, which
  6. customwas recrystallized from methanol/toluene

Sources & evidence

ORD record
ord-ddfd4788ff65454ea0ff79440b20cde0
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

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