p-Bromobenzenesulfonyl chloride → HCID 18698025, compound

HRID 2289526Notes

Reaction equation

HRID 2289526 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.[Br: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>[Br: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 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 18698021HCID 18698021, compound

Product 1

HCID 18698025HCID 18698025, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[1-(4-Pyrimidinyl)piperazin-4-ylcarbonyl]piperidine (385 mg) in dichloromethane (20 ml) was stirred at room temperature as a solid suspension and treated dropwise with 4-bromophenylsulphonyl chloride (385 mg) and triethylamine (0.4 ml) in dichloromethane (15 ml). The resulting clear yellow solution was stirred at the same temperature for a further 20 h and treated with saturated NaHCO3 solution (40 ml). The mixture was extracted twice with dichloromethane and the combined organic extracts washed twice each with water and brine dried over anhydrous MgSO4, filtered and evaporated under reduced pressure to a yellow solid. The solid was chromatographed through a 10 g silica bond elut prepacked column, eluting with 1% methanol, 1% ammonium hydroxide and 98% dichloromethane to give 1-(4-bromophenylsulphonyl)-4-[1-(4-pyrimidinyl)piperazin-4-ylcarbonyl]piperidine (209 mg; 30% yield based on the amine), as a colourless solid, mp 171-174° C.;

Workup

  1. extractionThe mixture was extracted twice with dichloromethane
  2. washthe combined organic extracts washed twice each with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure to a yellow solid
  6. customThe solid was chromatographed through a 10 g silica bond
  7. washeluting with 1% methanol, 1% ammonium hydroxide and 98% dichloromethane

Sources & evidence

ORD record
ord-dba6f1804148406491e13d78abf31e6d
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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