p-Bromobenzenesulfonyl chloride → HCID 18698025, compound

HRID 2288741Notes

Reaction equation

HRID 2288741 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.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[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; 1.4 mmol) in CH2Cl2 (20 ml) was stirred at room temperature as a solid suspension and treated dropwise with 4-Bromobenzenesulfonyl chloride (385 mg; 1.5 mmol) and Et3N (0.4 ml; 3 mmol) in CH2Cl2 (15 ml). The resulting clear yellow solution was stirred at the same temperature for a further 20 h then treated with saturated NaHCO3(aq) (40 ml). The mixture was extracted twice with CH2Cl2 and the combined organic extracts washed twice each with water and brine then 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% CH2Cl2 to give 1-(4-bromophenylsulphonyl)-4-(1-(4-pyrimidinyl)piperazin-4-ylcarbonyl)piperidine (209 mg; 30% yield based on the amine), a white solid, m.p. 171-174° C.;

Workup

  1. extractionThe mixture was extracted twice with CH2Cl2
  2. washthe combined organic extracts washed twice each with water and brine
  3. dry with materialthen dried 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% CH2Cl2

Sources & evidence

ORD record
ord-f538a8351d54482bb04fe0235745994d
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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