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

HRID 1267928Notes

Reaction equation

HRID 1267928 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 97.7%

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 hours. The mixture was then cooled, diluted with ethyl acetate (200 ml), washed with 2M aqueous hydrochloric acid (200 ml), dried (MgSO4), and concentrated to give the sub-title compound (4.05 g).

Workup

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

Sources & evidence

ORD record
ord-3e4f8af0f8224988a756ecc1dcb62e2a
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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