Reaction #217606

Reaction equation

5-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline

5-bromo-2-thiophenesulfonyl chloride

→

title product

5-Bromo-N-[2-chloro-5-(cis-3,5-dimethyl-1-piperazinyl)phenyl]-2-thiophenesulfonamide

Solvents

pyridine dichloromethane

Conditions

Workup

1. 1
   Otherquenched with methanol
2. 2
   Concentrationconcentrated in vacuo
3. 3
   Washwashed with methanol and 2M ammonia in methanol
4. 4
   ConcentrationThe combined basic fractions were concentrated in vacuo
5. 5
   Otherthe resulting residue was purified by column chromatography (FlashMaster) (gradient of dichloromethane to 4% metlianol:dichloromethane)

Procedure

A solution of 5-(cis-3,5-Dimethyl-1-piperazinyl)-2-chloroaniline (D34) (100 mg, 0.42 mmol) in pyridine:dichloromethane (1:1, 4 ml) was treated with 5-bromo-2-thiophenesulfonyl chloride (132 mg, 0.51 mmol). The solution was stirred at room temperature for 2 hours, quenched with methanol and concentrated in vacuo. The residue was applied to a SCX cartridge (Varian bond-elute, 5 g) and washed with methanol and 2M ammonia in methanol. The combined basic fractions were concentrated in vacuo and the resulting residue was purified by column chromatography (FlashMaster) (gradient of dichloromethane to 4% metlianol:dichloromethane) to afford the title product (D36). MS (ES+) m/e 464/466/468 [M+H]+.

Source