Dichloromethane → 1-(1-(5-Methoxy-2-methyl-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

HRID 1255996Notes

Reaction equation

HRID 1255996 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:13].[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CS(C)=O.O>[CH3:9][O:8][C:6]1[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]([CH3:13])=[C:2]([N:24]2[CH2:23][CH2:22][CH:21]([N:18]3[CH2:17][CH2:16][N:15]([CH3:14])[CH2:20][CH2:19]3)[CH2:26][CH2:25]2)[CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 7957071-Methyl-4-(piperidin-4-yl)piperazineHCID 184681411-Fluoro-5-methoxy-2-methyl-4-nitrobenzene2×

Product 1

HCID 580714941-(1-(5-Methoxy-2-methyl-4-nitrophenyl)piperidin-4-yl)-4-methylpiperazine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene (INTERMEDIATE 7, 0.370 g, 2.00 mmol), 1-methyl-4-(piperidin-4-yl)piperazine (0.367 g, 2.00 mmol), and potassium carbonate (0.415 g, 3.00 mmol) in DMSO (2.0 mL) were stirred at 80° C. for 15 h. DCM (20 mL) and water (20 mL) were added to the reaction mixture. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title product. (0.640 g, 92%).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9acda1fcfaf647bd8aa2d9ea987862aa
Source dataset
uspto-grants-2013_06
Patent number
US08461170B2

Reaction notes

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