Dimethyl Sulfoxide → 1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-[2-(methylsulfonyl)-ethyl]piperazine

HRID 419436Notes

Reaction equation

HRID 419436 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:15][CH2:14]1.[CH3:25][S:26]([CH:29]=[CH2:30])(=[O:28])=[O:27].CS(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:20][CH2:21][N:22]([CH2:30][CH2:29][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:23][CH2:24]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 19354Methyl vinyl sulfone2×HCID 594529121-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine

Product 1

HCID 594529281-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-[2-(methylsulfonyl)-ethyl]piperazineYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}piperazine (Example 112, step D) (0.050 g, 1.41 mmol) was taken up in THF (10 mL) and methylvinylsulfone (0.371 mL, 4.23 mmol) was added. DMSO was added to solubilize the starting material. Reaction was stirred overnight at rt. Reaction was not complete and over the next 3 days, 30 equivalents more methylvinylsulfone were added. Reaction was then stirred over the weekend. Poured reaction mixture onto prepackaged silica gel cartridge, dried by vacuum suction of air through cartridge and then flash chromatographed to give the title compound of step A (0.370 g, 57%). MS (M+H, ES+) 461.

Workup

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  4. stirringwas then stirred over the weekend
  5. additionPoured
  6. customreaction mixture onto prepackaged silica gel cartridge
  7. customdried by vacuum suction of air through cartridge
  8. customflash chromatographed

Sources & evidence

ORD record
ord-b7a51b57946044029b1210cca3a3ba24
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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