Benzenesulfonyl chloride → HCID 18432748, compound

HRID 2305366Notes

Reaction equation

HRID 2305366 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[F:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1[N:20]1[CH2:25][CH2:24][N:23]([C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[O:27])[CH2:22][CH2:21]1.C(N(CC)CC)C>ClCCl>[C:1]1([S:7]([N:31]2[CH2:30][CH2:29][N:28]([C:26]([N:23]3[CH2:22][CH2:21][N:20]([C:19]4[CH:18]=[CH:17][N:16]=[CH:15][C:14]=4[F:13])[CH2:25][CH2:24]3)=[O:27])[CH2:33][CH2:32]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18432750HCID 18432750, compound

Product 1

HCID 18432748HCID 18432748, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Phenylsulphonyl chloride (0.38 g) was added to a mixture of 1-[(3-fluoro-4-pyridyl)piperazin-4-ylcarbonyl]piperazine dihydrochloride (0.65 g) and triethylamine (1.5 ml) in dichloromethane (30 ml) at 5° C. The solution was stirred at 5° C. for 1 hour and at ambient temperature for 18 hours. The solution was evaporated to dryness. The residue was dissolved in dichloromethane (100 ml), and the solution was washed with water (3×10 ml), dried (Na2SO4) and evaporated. The residue was purified by chromatography on alumina (N32-63) using 0.1-0.3% methanol in dichloromethane as eluent. Recrystallisation from ethyl acetate/isohexane gave 1-phenylsulphonyl-4-[1-(3-fluoro-4-pyridyl)piperazin-4-ylcarbonyl]piperazine (0.49 g), as an off-white solid mp 143-145° C: NMR (CDCl3): 3.05 (t, 4H), 3.25 (t, 4H), 3.40 (m, 8H), 6.70 (dd, 1H), 7.60 (m, 3H), 7.78 (s, 2H), 8.20 (dd, 2H); m/z 434 (M+1).

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. washthe solution was washed with water (3×10 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on alumina (N32-63)
  7. customRecrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-19976988a03e497fa489b2baa3cab763
Source dataset
uspto-grants-2002_08
Patent number
US06440972B1

Reaction notes

Loading…