rel-(2R,6S)-2,6-dimethylpiperazine → HCID 59007101, compound

HRID 130401Notes

Reaction equation

HRID 130401 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][C@H:15]1[CH2:20][NH:19][CH2:18][C@@H:17]([CH3:21])[NH:16]1>CN1CCCC1=O.C(OCC)(=O)C>[CH3:14][C@H:15]1[NH:16][C@@H:17]([CH3:21])[CH2:18][N:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=2)[CH2:20]1

Participants

5

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 126437961-(4-Chloro-2-nitrophenyl)ethan-1-one

Product 1

HCID 59007101HCID 59007101, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(4-chloro-2-nitrophenyl)ethanone (WO 9322287) (700 mg, 3.5 mmol) and cis-2,6-dimethylpiperazine (1.2 g, 10.5 mmol) in 1-methyl-2-pyrrolidinone (12 ml) was heated at 160° C. in a microwave reactor for 40 min. The reaction mixture was cooled, diluted with ethyl acetate and washed with water (×3), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting 1:1 mixture of the title compound (D5) MS (ES+) m/e [M+H]+278 and 1-[4-chloro-2-(cis-3,5-dimethyl-1-piperazinyl)phenyl]ethanone MS (ES+) m/e [M+H]+267/269 was used crude in the next reaction.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water (×3), brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThe resulting 1:1 mixture of the title compound (D5) MS (ES+) m/e
  6. customin the next reaction

Sources & evidence

ORD record
ord-01d8d5e790b64d3fb087d21994a6a067
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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