Diethyl Ether → HCID 9870902, compound

HRID 2289520Notes

Reaction equation

HRID 2289520 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[N:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([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:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C.C(OCC)C>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([CH:27]3[CH2:32][CH2:31][N:30]([C:2]4[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[N:3]=4)[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

6

Reactant 4

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

Product 1

HCID 9870902HCID 9870902, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-methylpyrimidine (135 mg) was added to a solution of 1-(4-bromophenylsulphonyl)-4-(4-piperidylcarbonyl)piperazine (415 mg) in THF (15 ml) containing triethylamine (0.2 ml). The mixture was heated under reflux for 16 hours. After cooling, the THF was evaporated. The residue was treated with H2O(20 ml) and the aqueous extracted with ethyl acetate (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 dichloromethane/methanol/0.88 NH3 (96:3:1) gave an oil. Trituration with diethyl ether (10 ml) gave, as a colourless solid, l-(4-bromophenylsulphonyl)-4-[1-(2-methylpyrimidyl)-4-piperidylcarbonyl]piperazine (152 mg), mp 200-202° C.; NMR: 1.39-1.48 (m, 2H), 1.55-1.69 (m, 2H), 2.30 (s, 3H), 2.80-3.00 (m, 7H), 3.45-3.67 (m, 4H), 4.32 (m, 2H), 6.57 (d, 1H), 7.65 (d, 2H), 7.83 (d, 2H), 8.03 (d, 1H); EI-MS m/z 508 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder 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 ethyl acetate (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 dichloromethane/methanol/0.88 NH3 (96:3:1)
  13. customgave an oil

Sources & evidence

ORD record
ord-2cfb2cdf31f749adbfd2a13757e0805c
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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