1-(4-Bromophenyl)-4-methylpiperazine → 2-Chloro-5-[4-(4-methyl-piperazin-1-yl)-benzoyl]-benzenesulfonamide

HRID 873659Notes

Reaction equation

HRID 873659 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([C:25](N(OC)C)=[O:26])=[CH:23][C:22]=1[S:33](=[O:36])(=[O:35])[NH2:34]>O1CCCC1>[Cl:20][C:21]1[CH:32]=[CH:31][C:24]([C:25](=[O:26])[C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)=[CH:23][C:22]=1[S:33]([NH2:34])(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 118176751-(4-Bromophenyl)-4-methylpiperazineHCID 581073994-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamideHCID 178418306HCID 178418306, compound

Product 1

HCID 581074112-Chloro-5-[4-(4-methyl-piperazin-1-yl)-benzoyl]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.275 g of 1-(4-bromo-phenyl)-4-methyl-piperazine in tetrahydrofuran (90 mL) is cooled to −78° C. and treated with 1.44 mL of tert-butyllithium (1.5 M in pentane). After 15 min at −78° C. the reaction mixture is treated with 0.1 g of 4-chloro-N-methoxy-N-methyl-3-sulfamoyl-benzamide in tetrahydrofuran (3 mL). The temperature is then increased slowly to 0° C. and after completion the reaction is quenched by addition of 2 mL of saturated aqueous ammonium chloride and extracted with diethyl ether. The organics are washed with water, dried (magnesium sulfate) and concentrated to give 0.32 g of crude product which is purified by silica gel chromatography (95:5 methylene chloride/methanol) to give 2-chloro-5-[4-(4-methyl-piperazin-1-yl)-benzoyl]-benzenesulfonamide as a tan powder. MS (m/z): 394 (M+1); Rf 0.06 (95:5 methylene chloride/methanol).

Workup

  1. customafter completion the reaction is quenched by addition of 2 mL of saturated aqueous ammonium chloride
  2. extractionextracted with diethyl ether
  3. washThe organics are washed with water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give 0.32 g of crude product which
  7. customis purified by silica gel chromatography (95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-119d50e2b6ba47149490c3ec8a72b400
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

Loading…