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1,4-Dioxane → 1-(4-Amidino benzoyl)-4-(2-naphthalenesulfonyl)piperazine

HRID 278602
Notes
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Reaction equation

HRID 278602 reaction equation
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[S:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)(=[O:14])=[O:13].O1CCOCC1.Cl.[C:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)(=[NH:30])[NH2:29]>C(=O)(O)[O-].[Na+]>[C:28]([C:31]1[CH:39]=[CH:38][C:34]([C:35]([N:18]2[CH2:19][CH2:20][N:15]([S:12]([C:3]3[CH:4]=[CH:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:2]=3)(=[O:14])=[O:13])[CH2:16][CH2:17]2)=[O:36])=[CH:33][CH:32]=1)(=[NH:29])[NH2:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 226280844-Amidinobenzoylchloride hydrochlorideHCID 227218151-(Naphthalene-2-sulfonyl)piperazine hydrochloride

Product 1

HCID 183822251-(4-Amidino benzoyl)-4-(2-naphthalenesulfonyl)piperazineYield 52.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium Bicarbonate
Solvent

Procedure

To a solution of 1-(2-naphthalenesulfonyl)piperazine hydrochloride (313 mg) in sodium bicarbonate solution (20 ml)-dioxane (20 ml) was added 4-amidinobenzoyl chloride hydrochloride (219 mg) and the solution was stirred at room temperature for 30 minutes. The reaction solution was concentrated, to which were added dichloromethane and water. The organic layer was separated and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and the precipitate was filtered, washed with water and dried to give a colorless solid of the title compound (223 mg).

Workup

  1. concentrationThe reaction solution was concentrated, to which
  2. additionwere added dichloromethane and water
  3. customThe organic layer was separated
  4. extractionextracted with 1 N hydrochloric acid
  5. filtrationthe precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-39bb1184006143ad9ac88865de0648b5
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06359134B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes