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Dichloromethane → HCID 15409321, compound

HRID 1417955
Notes
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Reaction equation

HRID 1417955 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.[CH2:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN1CCCC1=O.C(Cl)(Cl)Cl.CCOC(C)=O>[CH2:15]([N:22]1[CH2:27][CH2:26][N:25]([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)[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 10987412Naphth[1,2-c]isoxazole, 3-chloro-4,5-dihydro-

Product 1

HCID 15409321HCID 15409321, compound

Reagents, catalysts & solvents 3

HCID 6212
Chloroform
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred mixture of 3-chloro-4,5-dihydronaphth[1,2-c]isoxazole (2.0 g, 9.75 mmol), 1-benzylpiperazine (17 ml, 97.5 mmol) and K2CO3 (2.7 g, 19.5 mmol) in 18 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 2 hours. 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 heptane. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to obtain a crude solid. The solid was collected, titrated with Et2O, recrystallized from Et2O and dried in vacuo (0.1 mm) at 85° C. to provide pure product, mp of 164°-166° C., homogeneous by TLC [silica, 1:1 EtOAc, Rf=0.80]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =345, EI, 70 eV) were consistent with the structure. The yield was 1.219 g (3.53 mmol, 36.24%).

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 heptane
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto obtain a crude solid
  10. customThe solid was collected
  11. customrecrystallized from Et2O
  12. customdried in vacuo (0.1 mm) at 85° C.
  13. customto provide pure product, mp of 164°-166° C.

Sources & evidence

ORD record
ord-5120a50d6ba44aaaaa1327dbc6f1b740
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05880121

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes