Piperazine → HCID 53643701, compound

HRID 1417956Notes

Reaction equation

HRID 1417956 reaction equation
Cl[C:2]1[O:6][N:5]=[C:4]2[C:7]3[C:12]([CH2:13][CH2:14][C:3]=12)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=3.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O.C(Cl)(Cl)Cl.C(Cl)Cl.CO>[N:17]1([C:2]2[O:6][N:5]=[C:4]3[C:7]4[C:12]([CH2:13][CH2:14][C:3]=23)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=4)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

8

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 54295927HCID 54295927, compound

Product 1

HCID 53643701HCID 53643701, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture of 3-chloro-8-methoxy-4,5-dihydronaphth[1,2-c]isoxazole (2.0 g, 8.51 mmol), piperazine (7.0 g, 80.6 mmol) and K2CO3 (2.4 g, 17.1 mmol) in 8.0 ml of N-methylpyrrolidinone under N2 was lowered into an oil bath preheated to 150° C. The mixture was heated while stirring under N2 for 20 minutes. At that time TLC [CH2Cl2 ] showed no starting material remained. The mixture was removed from the heating bath and allowed to cool to room temperature. Upon dilution of the reaction mixture with H2O, a solid precipitated which was collected and dried in vacuo to provide pure product, mp of 86°-88° C., homogeneous by TLC [silica, 1:1 CH3OH:CH2Cl2, Rf=0.37]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =285, EI, 70 eV) were consistent with the structure. The yield was 1.932 g (6.78 mmol, 79.66%).

Workup

  1. customwas lowered into an oil bath
  2. custompreheated to 150° C
  3. temperatureThe mixture was heated
  4. customThe mixture was removed from the heating bath
  5. customUpon dilution of the reaction mixture with H2O, a solid precipitated which
  6. customwas collected
  7. customdried in vacuo
  8. customto provide pure product, mp of 86°-88° C.

Sources & evidence

ORD record
ord-c869161a82b141238fdb43223dcf9a28
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

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