1-Phenylpiperazine → HCID 46182230, compound

HRID 386483Notes

Reaction equation

HRID 386483 reaction equation
[CH2:1]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]1([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH2:1]([N:8]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N:34]2[CH2:35][CH2:36][N:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:32][CH2:33]2)[CH:19]=1)[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 70961-PhenylpiperazineHCID 23676156Sodium t-butoxideHCID 46021782HCID 46021782, compound

Product 1

HCID 46182230HCID 46182230, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-benzyl-N-(3-bromo-phenyl)-benzene sulfonamide (25 mg, 0.06 mmol), 1-phenyl-piperazine (0.011 ml, 0.074 mmol), palladium acetate (1 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (2 mg) and sodium tert-butoxide (21 mg, 0.22 mmol) in dioxane (4 ml) were refluxed overnight. The reaction was quenched with water (5 ml) and extracted with dichloromethane (3×6 ml). The organic extracts were combined, filtered then concentrated in vacuo and the residues purified by preparative TLC (SiO2) eluting with dichloromethane to afforded the title compound as a yellow solid (23 mg, 77%) HPLC retention time 9.4 min. Mass spectrum (ES+) m/z 484 (M+H).

Workup

  1. customThe reaction was quenched with water (5 ml)
  2. extractionextracted with dichloromethane (3×6 ml)
  3. filtrationfiltered
  4. concentrationthen concentrated in vacuo
  5. customthe residues purified by preparative TLC (SiO2)
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-76d5cfdcf4b74ea59e58f80cc9f633a9
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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