Potassium Carbonate → 1-(3-((6-Chloro-2-naphthyl)sulfonyl)propionyl)piperazine

HRID 493693Notes

Reaction equation

HRID 493693 reaction equation
[N:1]1([C:7]([O:9]C(C)(C)C)=O)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:25]([CH2:28][CH2:29]C(O)=O)(=[O:27])=[O:26])[CH:19]=[CH:18]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(N(CC)CC)C>[Cl:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:25]([CH2:28][CH2:29][C:7]([N:1]1[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]1)=[O:9])(=[O:27])=[O:26])[CH:19]=[CH:18]2

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 111973043-(6-Chloro-2-naphthyl)sulfonylpropionic acid

Product 1

HCID 231308831-(3-((6-Chloro-2-naphthyl)sulfonyl)propionyl)piperazineYield 88.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

tert-Butyl 1-piperazine carboxylate (5.0 g) was dissolved in dichloromethane (20 mL), and triethylamine (3.8 mL) was added thereto. With ice cooling, 3-((6-chloro-2-naphthyl)sulfonyl)propionic acid (8.0 g), HOBt (4.5 g) and WSC (5.7 g) were added thereto, and the mixture was mixed at room temperature for 16 hours. The reaction solution was basified with an aqueous potassium carbonate solution, then extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was dissolved in trifluoroacetic acid (25 mL) and mixed at room temperature for 1 hour. After concentrating the reaction solution, the residue was basified with an aqueous potassium carbonate solution and extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, and then the solvent was concentrated to give the title compound (8.7 g) as a pale brown oily matter.

Workup

  1. additionthe mixture was mixed at room temperature for 16 hours
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. dissolutionthe residue was dissolved in trifluoroacetic acid (25 mL)
  6. additionmixed at room temperature for 1 hour
  7. concentrationAfter concentrating the reaction solution
  8. extractionextracted with chloroform
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-0e093edae32a430484f90e0f8b33d407
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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