Ethanol → HCID 69699735, compound

HRID 352895Notes

Reaction equation

HRID 352895 reaction equation
C(O)C.O1CCCC1.Cl.[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([S:21]([N:24]1[CH2:29][CH2:28][N:27]([C:30](=[O:43])[C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)=[CH:33][CH:32]=3)[CH:26]([C:44]([O:46]CC)=[O:45])[CH2:25]1)(=[O:23])=[O:22])[CH:15]=[CH:14]2.[OH-].[Na+]>O>[ClH:10].[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([S:21]([N:24]1[CH2:29][CH2:28][N:27]([C:30](=[O:43])[C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)=[CH:33][CH:32]=3)[CH:26]([C:44]([OH:46])=[O:45])[CH2:25]1)(=[O:23])=[O:22])[CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22710121HCID 22710121, compound

Product 1

HCID 69699735HCID 69699735, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixed solvent of ethanol (1 ml), tetrahydrofuran (1 ml) and water (1 ml), 4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-ethoxycarbonyl-1-[4-(pyridin-4-yl)benzoyl]piperazine hydrochloride (152 mg) obtained in Example A-2 was dissolved under ice cooling, followed by the dropwise addition of a 1N aqueous solution of sodium hydroxide. The reaction mixture was stirred at room temperature for 90 minutes. After concentration under reduced pressure, 1N hydrochloric acid was added to the reaction mixture to make it weakly acidic. The colorless solid so precipitated was collected by filtration, followed by drying, whereby the title compound (62 mg, 42%) was obtained as a colorless solid.

Workup

  1. dissolutionwas dissolved under ice cooling
  2. concentrationAfter concentration under reduced pressure, 1N hydrochloric acid
  3. additionwas added to the reaction mixture
  4. customThe colorless solid so precipitated
  5. filtrationwas collected by filtration
  6. customby drying

Sources & evidence

ORD record
ord-4ec66afb21814364831dbe6a990b02b2
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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