p-Bromobenzenesulfonyl chloride → HCID 6734934, compound

HRID 427442Notes

Reaction equation

HRID 427442 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([S:27]([C:24]3[CH:25]=[CH:26][C:21]([Br:20])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazine

Product 1

HCID 6734934HCID 6734934, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(4-pyridyl)piperazine (0.49 g) and triethylamine (0.7 ml) in dry dichloromethane (20 ml) was treated slowly with a solution of 4-bromophenylsulphonyl chloride (0.77 g) in dry dichloromethane (10 ml). The reaction mixture was then stirred under argon for 2 hours. The dichloromethane solvent was removed by evaporation and the residue dissolved in ethyl acetate. The organic extracts were washed with water, brine, dried (MgSO4) and evaporated to yield a white crystalline solid which was recrystallised from ethyl acetate to give 1-(4-pyridyl)-4-(4-bromophenylsulphonyl)piperazine (0.84 g) as a solid, m.p. 199-200° C.: microanalysis, found: C, 47.3; H, 4.1; N, 10.9%; C15H16BrN3O2S requires: C, 47.1; H, 4.22; N, 11.0%; NMR: (CDCl3) 3.13(t,4H), 3.42(t,4H), 6.62(dd,2H), 7.67(q,4H), 8.29(d,2H): MS: m/z 382 (MH)−.

Workup

  1. customThe dichloromethane solvent was removed by evaporation
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto yield a white crystalline solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d9ce987aa31c44f39775564a23a78877
Source dataset
uspto-grants-2001_11
Patent number
US06313127B1

Reaction notes

Loading…