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

HRID 1419583Notes

Reaction equation

HRID 1419583 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14]1.N1C=CC=CC=1>ClCCl>[CH2:19]([N:16]1[CH2:15][CH2:14][N:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:18][CH2:17]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

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

Product 1

HCID 21935090N-[2-(4-Benzylpiperazin-1-yl)phenyl]methanesulfonamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.91 mL, 11.7 mmol) was added to a cooled (0° C.) solution of 1-(2-aminophenyl)-4-benzylpiperazine (2.61 g, 9.8 mmol) and pyridine (0.95 mL, 11.7 mmol) in dichloromethane (30 mL) and the mixture was stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure and triethylamine (1.4 mL) was added. The mixture was azeotroped with xylene, diluted with ethyl acetate and washed with aqueous potassium carbonate (saturated, 3×). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH (99:1) to give the title compound as yellow oil (2.83 g, 84%). δH (250 MHz, CDCl3) 7.88-7.80 (1H, br s), 7.51 (1H, dd, J 1.6, 8.0 Hz), 7.34-7.27 (5H, m), 7.25 (1H, dd, J 1.6, 7.5 Hz), 7.16 (1H, dt, J 1.6, 7.5 Hz), 7.07 (1H, dt, J 1.7, 7.6 Hz), 3.59 (2H, s), 3.04 (3H, s), 2.90-2.85 (4H, m), and 2.66-2.60 (4H, br s).

Workup

  1. customThe solvent was evaporated under reduced pressure and triethylamine (1.4 mL)
  2. additionwas added
  3. customThe mixture was azeotroped with xylene
  4. additiondiluted with ethyl acetate
  5. washwashed with aqueous potassium carbonate (saturated, 3×)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluting with CH2Cl2 /MeOH (99:1)

Sources & evidence

ORD record
ord-7eb11ddc9c6448518d5d42875336aa18
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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