Dimethyl Sulfoxide → HCID 117666904, compound

HRID 1526230Notes

Reaction equation

HRID 1526230 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.Cl.Cl.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]1[CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][C@H:15]1[CH2:20][OH:21]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1176672471448242-43-0

Product 1

HCID 117666904HCID 117666904, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-fluoro-4-nitrobenzene (418 μL), [(2S)-1-methylpiperazin-2-yl]methanol dihydrochloride (0.8 g), potassium carbonate (2.45 g), and dimethylsulfoxide (8 mL) was stirred at 120° C. for 3 hours. To the reactant were added water and ethyl acetate, followed by liquid separation. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate) to obtain [(2S)-1-methyl-4-(4-nitrophenyl)piperazin-2-yl]methanol (590 mg) as a yellow solid.

Workup

  1. customfollowed by liquid separation
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; ethyl acetate)

Sources & evidence

ORD record
ord-5caac05e2eae45ca94546d926e97c182
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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