Hydrochloric Acid → [7-Chloro-2-oxo-4-phenyl-6-[(4-phenylpiperazin-1-yl)methyl]-2h-chromen-3-yl]acetic acid

HRID 488880Notes

Reaction equation

HRID 488880 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:8]([CH2:14][C:15]([O:17]CC)=[O:16])[C:9](=[O:13])[O:10]2)=[CH:5][C:4]=1[CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>C(O)C>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:8]([CH2:14][C:15]([OH:17])=[O:16])[C:9](=[O:13])[O:10]2)=[CH:5][C:4]=1[CH2:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131725236Ethyl [7-chloro-2-oxo-4-phenyl-6-[(4-phenylpiperazin-1-yl)methyl]-2h-chromen-3-yl]acetate.hydrochloride

Product 1

HCID 22267205[7-Chloro-2-oxo-4-phenyl-6-[(4-phenylpiperazin-1-yl)methyl]-2h-chromen-3-yl]acetic acidYield 96.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Ethyl [7-chloro-2-oxo-4-phenyl-6-[(4-phenylpiperazin-1-yl)methyl]-2H-chromen-3-yl]acetate.hydrochloride (40 g) was suspended in ethanol (120 ml), and combined with a 2 N aqueous solution of sodium hydroxide (144.5 ml). A yellow clear solution obtained by stirring at 70° C. for 1 hour was added dropwise to a mixture solution of ethanol (40 ml) and 6 N hydrochloric acid (49.4 ml) over 45 minutes. The reaction solution was adjusted to pH 5.5 to 6.0 with sodium hydrogen carbonate at 40° C. After pH became stable, the mixture was stirred at 35 to 40° C. internal temperature for 15 minutes, and cooled to room temperature, and stirred at room temperature for 30 minutes. The crystal formed was filtered and washed with 30% ethanol to obtain the title compound (34 g, yield: 96%) as a white crystal.

Workup

  1. customA yellow clear solution obtained
  2. stirringthe mixture was stirred at 35 to 40° C. internal temperature for 15 minutes
  3. temperaturecooled to room temperature
  4. stirringstirred at room temperature for 30 minutes
  5. customThe crystal formed
  6. filtrationwas filtered
  7. washwashed with 30% ethanol

Sources & evidence

ORD record
ord-904ee024d0f248b78f0653a1e239daa3
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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