4-Chlorobenzenesulfonyl chloride → HCID 18697988, compound

HRID 2289525Notes

Reaction equation

HRID 2289525 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH2:9][CH2:8]2)=[N:3][CH:2]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:18]2[CH2:19][CH2:20][CH:15]([C:13]([N:10]3[CH2:9][CH2:8][N:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][N:3]=4)[CH2:12][CH2:11]3)=[O:14])[CH2:16][CH2:17]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18698021HCID 18698021, compound

Product 1

HCID 18697988HCID 18697988, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[1-(4-Pyrimidinyl)piperazin-4-ylcarbonyl]piperidine (412 mg) was dissolved in dichloromethane (16 ml), cooled in an ice bath, stirred and treated dropwise with a mixture of 4-chlorophenylsulphonyl chloride (338 mg) and triethylamine (0.3 ml) in dichloromethane (16 ml). The reaction mixture was allowed to reach room temperature and stirred for 18 h before treating with saturated NaHCO3 solution. This mixture was extracted twice with dichloromethane. The combined organic extracts were washed twice with water and brine, dried over MgSO4, filtered and evaporated under reduced pressure to a yellow solid. The solid thus obtained was chromatographed through a 10 g silica "bond elut" prepacked column, eluting with 1% methanol, 1% ammonium hydroxide and 98% dichloromethane to obtain 1-(4-chlorophenylsulphonyl)-4-[1-(4-pyrimidinyl)piperazin-4-ylcarbonyl]piperidine (178 mg; 26% yield based on the amine), as a white solid, mp 125-128° C.;

Workup

  1. temperaturecooled in an ice bath
  2. customto reach room temperature
  3. stirringstirred for 18 h
  4. extractionThis mixture was extracted twice with dichloromethane
  5. washThe combined organic extracts were washed twice with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure to a yellow solid
  9. customThe solid thus obtained
  10. customwas chromatographed through a 10 g silica "bond
  11. washeluting with 1% methanol, 1% ammonium hydroxide and 98% dichloromethane

Sources & evidence

ORD record
ord-539b8013fbad4913bdee5b359473ad9e
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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