Diethyl Ether → HCID 86755526, compound

HRID 2288735Notes

Reaction equation

HRID 2288735 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[N:3]=1.BrC1C=CC(S([N:19]2[CH2:24][CH2:23][N:22]([C:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=O)=O)=CC=1.C(N(CC)CC)C.CCOCC>C1COCC1>[CH3:8][C:4]1[N:3]=[C:2]([N:30]2[CH2:31][CH2:32][CH:27]([C:25]([N:22]3[CH2:23][CH2:24][NH:19][CH2:20][CH2:21]3)=[O:26])[CH2:28][CH2:29]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 10669572HCID 10669572, compound

Product 1

HCID 86755526HCID 86755526, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-methylpyrimidine (135 mg) was added to a solution of 1-(4-bromophenylsulphonyl)-4-(piperidin-4-ylcarbonyl )piperazine (415 mg) in THF (15 ml) containing triethylamine (0.2 ml). The mixture was heated at reflux for 16 hours. After cooling, the THF was evaporated. The residue was treated with H2O (20 ml) and the aqueous extracted with EtOAc (3×20 ml). The combined organic phases were washed with saturated brine (1×20 ml) dried and evaporated to give an oil which was purified by chromatography on silica gel. Elution with CH2Cl2 /MeOH/0.88NH3 (96:3:1) gave an oil. Trituration with Et2O (10 ml) gave, as a colourless solid, 1-(4-bromophenylsulphonyl) 4-(4-(1-(2-methylpyrimidyl)piperidin-4-ylcarbonyl)piperazine (152 mg), mp 200-202° C.;

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling
  4. customthe THF was evaporated
  5. additionThe residue was treated with H2O (20 ml)
  6. extractionthe aqueous extracted with EtOAc (3×20 ml)
  7. washThe combined organic phases were washed with saturated brine (1×20 ml)
  8. customdried
  9. customevaporated
  10. customto give an oil which
  11. customwas purified by chromatography on silica gel
  12. washElution with CH2Cl2 /MeOH/0.88NH3 (96:3:1)
  13. customgave an oil

Sources & evidence

ORD record
ord-08b3b2d8da4f47c4b88d2690675a4925
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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