Piperazine → HCID 15409320, compound

HRID 1417954Notes

Reaction equation

HRID 1417954 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]=[CH:9][CH:8]=3.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O.C(Cl)(Cl)Cl.C(Cl)Cl.CO>[N:15]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]=[CH:9][CH:8]=4)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

8

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 10987412Naphth[1,2-c]isoxazole, 3-chloro-4,5-dihydro-

Product 1

HCID 15409320HCID 15409320, compound

Reagents, catalysts & solvents 4

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

Procedure

A stirred mixture of 3-chloro-4,5-dihydronaphth[1,2-c]isoxazole (5.0 g, 24.4 mmol), piperazine(34.2 g, 397.7 mmol) and K2CO3 (6.73 g, 48.7 mmol) in 40 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 45 minutes. At that time, TLC (CH2Cl2) showed no remaining starting material. The mixture was removed from the heating bath, allowed to cool to room temperature and extracted with Et2O. This organic phase was washed twice with H2O, dried over MgSO4, filtered and concentrated in vacuo to obtain a crude solid. The solid was collected, recrystallized from heptane/Et2O and dried in vacuo (0.1 mm) at 85° C. to provide pure product, mp of 97°-99° C., homogeneous by TLC [silica, 1:1 CH3OH:CH2Cl2, Rf=0.35]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =255, EI, 70 ev) were consistent with the structure. The yield was 3.372 g (13.22 mmol, 54.19%).

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. extractionextracted with Et2O
  6. washThis organic phase was washed twice with H2O
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto obtain a crude solid
  11. customThe solid was collected
  12. customrecrystallized from heptane/Et2O
  13. customdried in vacuo (0.1 mm) at 85° C.
  14. customto provide pure product, mp of 97°-99° C.

Sources & evidence

ORD record
ord-49e3cbb6d7104d18886c202e8f79819b
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

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