Dimethyl Sulfoxide → Tert-butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylate

HRID 2298073Notes

Reaction equation

HRID 2298073 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 53763997Tert-butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-2-methyl-1-nitrobenzene (2 g), piperazine-1-carboxylic acid tert-butyl ester (4.8 g), potassium carbonate (3.57 g) and dimethyl sulfoxide (20 ml) were heated together at 80 ° C. under nitrogen for 15 h. The mixture was then cooled, diluted with ethyl acetate (200 ml), washed with 2N aqueous hydrochloric acid (200 ml), dried (MgSO4), and concentrated to give the subtitle compound (4.10 g).

Workup

  1. temperatureThe mixture was then cooled
  2. washwashed with 2N aqueous hydrochloric acid (200 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-11bf63a9708241d68b9f32ba357d9d6f
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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