Dichloromethane → cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazine

HRID 1826584Notes

Reaction equation

HRID 1826584 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][C@@H:14]([CH3:18])[NH:13]1.ClCCl>O>[CH3:11][C@H:12]1[NH:13][C@@H:14]([CH3:18])[CH2:15][N:16]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:17]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9590p-FluoronitrobenzeneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 7059963cis-3,5-Dimethyl-1-(4-nitrophenyl)piperazineYield 103.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A suspension of 6.74 g (47.8 mmol) of 4-fluoro-nitro-benzene and 10.91 g (95.5 mmol) of cis-2,6-dimethyl-piperazine is heated at 45° C. for 1 hour. The reaction mixture is cooled and shaken with dichloromethane and water. The organic layer is dried (magnesium sulfate) and concentrated to give 11.62 g (>100%) of the product as a solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. dry with materialThe organic layer is dried (magnesium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c345d70e59794d199abe9ba7552457a8
Source dataset
uspto-grants-2006_05
Patent number
US07053070B2

Reaction notes

Loading…