Pyridine → N-[2-(4-Benzylpiperazin-1-yl)phenyl]methanesulfonamide

HRID 228069Notes

Reaction equation

HRID 228069 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C([O-])(O)=O.[Na+]>C(Cl)CCl>[CH3:27][S:28]([NH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 45188322-(4-Benzylpiperazin-1-yl)aniline

Product 1

HCID 21935090N-[2-(4-Benzylpiperazin-1-yl)phenyl]methanesulfonamideYield 95.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a round-bottomed flask equipped with magnetic stirring was added 2-[4-benzylpiperazinyl]phenylamine (34 g, 127 mmol) in ClCH2CH2Cl (100 mL) and pyridine (12 mL, 140 mmol). The reaction mixture was stirred for 5 min. To the reaction was added methanesulfonyl chloride (Aldrich) (11 mL, 139 mmol), and the reaction mixture was heated at reflux for 18 h. After cooling to RT a satd soln of NaHCO3 (50 mL) was added. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (2×50 mL). All organic fractions were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the sulfonamide as yellow oil (42 g). MS (ESI, pos. Ion) m/z: 346 (M+H); MS (ESI, neg. Ion) m/z: 344 (M−H). Calc'd for C18H23N3O2S: 345.15.

Workup

  1. customTo a round-bottomed flask equipped
  2. stirringThe reaction mixture was stirred for 5 min
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 18 h
  5. additionwas added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×50 mL)
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40296e2d4c8242f880825b89f84e6a26
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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