Piperazine → 1-(3-(Methylsulfonyl)phenyl)piperazine

HRID 1070728Notes

Reaction equation

HRID 1070728 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][S:8]([C:4]1[CH:3]=[C:2]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:7]=[CH:6][CH:5]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 4837PiperazineHCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-HCID 23676156Sodium t-butoxide

Product 1

HCID 129889541-(3-(Methylsulfonyl)phenyl)piperazine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-bromo-3-methanesulfonyl-benzene (0.8 g), piperazine (1 g), sodium tert-butoxide (0.5 g) BINAP (42 mg) and [Pd2(dba)3 (38 mg) in toluene (7 ml) was heated under argon at 80° C. for 24 h. After cooling to room temperature, the solvent was evaporated to dryness. The crude material was purified by flash chromatography on silica gel using EtOAc. Yield 0.48 g: MS m/z (rel. intensity, 70 eV) 240 (M+, 17), 199 (12), 198 (bp), 119 (9), 56 (7).

Workup

  1. customthe solvent was evaporated to dryness
  2. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-12fce80713fe436d83fad2907efde3e6
Source dataset
uspto-grants-2005_06
Patent number
US06903120B2

Reaction notes

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