Chlorosuccinimide → HCID 18432760, compound

HRID 2305355Notes

Reaction equation

HRID 2305355 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br: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>[Br: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 18432749HCID 18432749, compound

Product 1

HCID 18432760HCID 18432760, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Chlorosuccinimide (3.06 g) was added to a stirred suspension of 1-(4-bromophenylsulphonyl)-4-[1-(4-pyridyl)piperazin-4-ylcarbonyl]piperazine (10.1 g) in acetonitrile (350 ml) at 20° C. The mixture was stirred for 48 hours and the acetonitrile evaporated. Water (200 ml) was added to the mixture and the aqueous phase was extracted with dichloromethane (3×200 ml). The organic extracts were combined, dried and evaporated, and the residue purified by column chromatography on silica gel, eluting with dichloromethane:methanol (97:3) to give a foam on evaporation. Trituration with diethyl ether (200 ml) gave 1-(4-bromophenylsulphonyl)-4-[1-(3-chloro-4-pyridyl)piperazin4-ylcarbonyl]piperazine as a cream-coloured solid (7.82 g): mp 194-195° C.: 1HNMR (CDCl3); 3.04 (t, 4H), 3.18 (t, 4H), 3.42 (m, 8H), 6.78 (d, 1H), 7.91 (d, 2H), 7.70 (d, 2H), 8.34 (d, 2H), 8.42 (s, 1H); EI-MS m/z 528 (M+H).

Workup

  1. customthe acetonitrile evaporated
  2. additionWater (200 ml) was added to the mixture
  3. extractionthe aqueous phase was extracted with dichloromethane (3×200 ml)
  4. customdried
  5. customevaporated
  6. customthe residue 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-c91b70e7acb14f29ac36a1f880034091
Source dataset
uspto-grants-2002_08
Patent number
US06440972B1

Reaction notes

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