4-Chlorobenzenesulfonyl chloride → HCID 18697988, compound

HRID 2288740Notes

Reaction equation

HRID 2288740 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.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[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 6344DichloromethaneSolvent3×

Procedure

4-(1-(4-Pyrimidinyl)piperazin-4ylcarbonyl)piperidine (412 mg; 1.5 mmol) was dissolved in CH2Cl2 (16 ml), cooled in an ice bath, stirred and treated dropwise with a mixture of 4-Chlorobenzenesulfonyl chloride (338 mg; 1.6 mmol) and Et3N (0.3 ml; 2 mmol) in CH2Cl2 (16 ml). The reaction mixture was allowed to reach room temperature and stirred thus for 18 h before treating with saturated NaHCO3 (aq) This mixture was then extacted twice with CH2Cl2. The combined organic extracts were washed twice each 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% ammonimum hydroxide and 98% CH2Cl2 to obtain 1-(4-chlorophenylsulphonyl)-4-(1-(4-pyrimidinyl)piperazin-4-ylcarbonyl)piperidine (178 mg; 26% yield based on the amine ), a white solid, m.p. 125-128° C.;

Workup

  1. temperaturecooled in an ice bath
  2. customto reach room temperature
  3. stirringstirred thus for 18 h
  4. washThe combined organic extracts were washed twice each with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure to a yellow solid
  8. customThe solid thus obtained
  9. customwas chromatographed through a 10 g silica "bond
  10. washeluting with 1% methanol, 1% ammonimum hydroxide and 98% CH2Cl2

Sources & evidence

ORD record
ord-0a04e3740b914cada14f881f469b1642
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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