Methanesulfonyl chloride → N-{4-[4-(Pyridin-4-yl)piperazin-1-yl]phenyl}methanesulfonamide

HRID 2232396

Reaction equation

HRID 2232396 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[N:22]1[CH:23]=[CH:24][C:19]([N:16]2[CH2:15][CH2:14][N:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=3)[CH2:18][CH2:17]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 108904611-(4-Aminophenyl)-4-(4-pyridyl)piperazine

Product 1

HCID 15735407N-{4-[4-(Pyridin-4-yl)piperazin-1-yl]phenyl}methanesulfonamideYield 42.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.50 g) was added dropwise to a stirred solution of 1-(4-aminophenyl)-4-(4-pyridyl)piperazine (1.00 g) in dry pyridine (10 ml) at room temperature. The mixture was stirred at room temperature for 20 hours and then evaporated. The residue was dissolved in water and the solution was basified with sodium bicarbonate solution and allowed to stand for 2 hours. The solid was filtered off, washed with water, dried and crystallised from methanol/ethyl acetate to give the title compound (0.55 g), m.p. 230°-232° C. Found: C,57.80; H,6.07; N,16.89. C16H20N4O2S requires: C,57.81; H,6.06; N,16.85%.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. waitto stand for 2 hours
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customdried
  7. customcrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-4c8f5d71fb2241cbb014594916a86f98
Source dataset
uspto-grants-1988_11
Patent number
US04788196

Linked notes

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