Hydrochloric Acid → HCID 68526888, compound

HRID 884180Notes

Reaction equation

HRID 884180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:5]([NH:7][C:8]1[CH:36]=[CH:35][C:11]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:25][CH2:24]3)=[O:22])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1)=[O:6].[OH-].[Na+].O.Cl>C1COCC1.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]([N:23]3[CH2:24][CH2:25][N:26]([CH2:29][C:30]([OH:32])=[O:31])[CH2:27][CH2:28]3)=[O:22])=[CH:17][CH:18]=2)=[CH:35][CH:36]=1)=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68527352HCID 68527352, compound

Product 1

HCID 68526888HCID 68526888, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[4-(3-{4-[4-(3,4-dichlorobenzoylamino)phenoxy]phenyl}propionyl)piperazin-1-yl]acetate (0.493° g, 0.843 mmol) in THF (5 mL) and ethanol (5 mL) were added 5 M aqueous sodium hydroxide (0.253 mL, 1.27 mmol) and water (1 mL), and the resulting solution was refluxed for 1 hour. This reaction solution was concentrated under reduced pressure, and the residue was dissolved in 50% aqueous ethanol. To the resulting solution was added 5 M hydrochloric acid (0.253 mL, 1.27 mmol), and the obtained solid was collected by filtration. To this solid was dissolved in ethanol (10 mL) and 5 M hydrochloric acid (0.3 mL) by heating. The solvent was then evaporated, and the obtained solid was recrystallized from ethanol-diethyl ether, to thereby yield 0.381 g of the title compound.

Workup

  1. temperaturethe resulting solution was refluxed for 1 hour
  2. concentrationThis reaction solution was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in 50% aqueous ethanol
  4. filtrationthe obtained solid was collected by filtration
  5. dissolutionTo this solid was dissolved in ethanol (10 mL)
  6. temperature5 M hydrochloric acid (0.3 mL) by heating
  7. customThe solvent was then evaporated
  8. customthe obtained solid was recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-e605d93feaba4e34ba46d9de4d6dee74
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

Loading…