Chlorosuccinimide → HCID 18432755, compound

HRID 2305365Notes

Reaction equation

HRID 2305365 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1>C(#N)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:20][CH2:21][N:22]([C:25]([N:27]3[CH2:28][CH2:29][N:30]([C:33]4[CH:34]=[CH:35][N:36]=[CH:37][C:38]=4[Cl:1])[CH2:31][CH2:32]3)=[O:26])[CH2:23][CH2:24]2)(=[O:17])=[O:18])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 18432762HCID 18432762, compound

Product 1

HCID 18432755HCID 18432755, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (4.05 g) was added to a stirred suspension of 1-(4-fluorophenylsulphonyl)-4-[1-(4-pyridyl)piperazin-4-ylcarbonyl]piperazine (12.45 g) in acetonitrile (500 mL) at 20° C. The mixture was stirred for 48 hours and the acetonitrile evaporated. Water (200 mL) was added to the residue and the aqueous phase extracted with dichloromethane (3×200 mL). The organic extracts were dried and evaporated. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol (97:3) to give a foam on evaporation. Trituration with diethyl ether (250 mL) gave 1-(4-fluorophenylsulphonyl)-4-[1-(3-chloro-4-pyridyl)piperazin-4-ylcarbonyl]piperazine as a pale yellow solid (9.18 g): mp 143-144° C.: NMR (CDCl3): 3.04(t, 4H), 3.15(t, 4H), 3.41(t, 8H), 6.78(d, 1H), 7.21(d, 2H), 7.78(m, 2H), 8.33(d, 1H), 8.42(s, 1H); EI-MS m/z 468(M+H).

Workup

  1. customthe acetonitrile evaporated
  2. additionWater (200 mL) was added to the residue
  3. extractionthe aqueous phase extracted with dichloromethane (3×200 mL)
  4. customThe organic extracts were dried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with dichloromethane:methanol (97:3)
  8. customto give a foam
  9. customon evaporation

Sources & evidence

ORD record
ord-25e490a606204b82bce71dda84d5af8c
Source dataset
uspto-grants-2002_08
Patent number
US06440972B1

Reaction notes

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