Dichloromethane → HCID 86753857, compound

HRID 1417959Notes

Reaction equation

HRID 1417959 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.[F:17][C:18]1[CH:32]=[CH:31][C:21]2[C:22]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[N:23][O:24][C:20]=2[CH:19]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN1CCCC1=O.C(Cl)(Cl)Cl.CCOC(C)=O.CCCCCCC>[F:17][C:18]1[CH:32]=[CH:31][C:21]2[C:22]([CH:25]3[CH2:26][CH2:27][N:28]([N:5]4[C:4]5[C:7]6[C:12]([CH2:13][CH2:14][C:3]=5[CH2:2][O:6]4)=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[CH:8]=6)[CH2:29][CH2:30]3)=[N:23][O:24][C:20]=2[CH:19]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 54295927HCID 54295927, compound

Product 1

HCID 86753857HCID 86753857, compound

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolventHCID 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), 4-(6-fluorobenzisoxazol-3-yl)-piperidine (2.8 g, 12.76 mmol) and K2CO3 (2.35 g, 17.02 mmol) in 10 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 90 minutes. At that time TLC (CH2Cl2) showed no remaining starting material. 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, dried, dissolved in CH2Cl2 and filtered through neutral alumina. The fractions containing desired product were combined and concentrated, and the resultant solid obtained was triturated with Et2O to provide a solid, mp of 181°-183° C., homogeneous by TLC [silica, 2:1 Heptane:EtOAc, Rf=0.15]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =419, EI, 70 eV) were consistent with the structure. The yield was 1.1318 g (2.70 mmol, 31.70%).

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
  8. dissolutiondissolved in CH2Cl2
  9. filtrationfiltered through neutral alumina
  10. additionThe fractions containing desired product
  11. concentrationconcentrated
  12. customthe resultant solid obtained
  13. customwas triturated with Et2O
  14. customto provide a solid, mp of 181°-183° C.

Sources & evidence

ORD record
ord-e6aaf71a61634b43ad43cb68b899b710
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

Loading…