Methanesulfonyl chloride → N-[4-(4-Acetylpiperazin-1-yl)phenyl]methanesulfonamide

HRID 2291571Notes

Reaction equation

HRID 2291571 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:17][S:18](Cl)(=[O:20])=[O:19]>>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:18]([CH3:17])(=[O:20])=[O:19])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one

Product 1

HCID 21278916N-[4-(4-Acetylpiperazin-1-yl)phenyl]methanesulfonamide

Procedure

To 1-Acetyl-4-(4-aminophenyl)piperazine (10.96 g) in ice-cold pyridine (100 ml) was added methanesulphonyl chloride (6.3 g) dropwise. The mixture was then stirred at ambient temperature overnight and the pyridine removed in vacuo. The residue was triturated with aqueous sodium bicarbonate, and the resulting solid was washed (water) and crystallized from methanol/ethyl acetate (charcoal). The yield of the title compound was 9.97 g, m.p. 165°-7°.

Workup

  1. customthe pyridine removed in vacuo
  2. customThe residue was triturated with aqueous sodium bicarbonate
  3. washthe resulting solid was washed (water)
  4. customcrystallized from methanol/ethyl acetate (charcoal)

Sources & evidence

ORD record
ord-a69fa9d0bcfa49dba09bd20e72174256
Source dataset
uspto-grants-1989_01
Patent number
US04797401

Reaction notes

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