Potassium Carbonate → HCID 70064071, compound

HRID 1417957Notes

Reaction equation

HRID 1417957 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[CH2:23][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)[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 68163Hexahydro-1,4-diazepineHCID 54295927HCID 54295927, compound

Product 1

HCID 70064071HCID 70064071, 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 (2.66 g, 11.32 mmol), homopiperazine (11.40 g, 113.2 mol) and K2CO3 (3.13 g, 22.68 mmol) in 10.0 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, allowed to cool to room temperature and diluted with H2O, which caused a solid to precipitate. The crude solid was dried, recrystallized from Et2O and dried in vacuo (0.1 mm) at 85° C., to provide pure product, mp of 106°-109° C., homogeneous by TLC [silica, 1:1 CH3OH:CH2Cl2, Rf=0.18]. The IR (CHCl3), NMR (CDCl3) and Mass Spectrum (M+ =299, EI, 70 eV) were consistent with the structure. The yield was 1.7948 g (6.00 mmol, 53.03%).

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. additiondiluted with H2O, which
  6. customto precipitate
  7. customThe crude solid was dried
  8. customrecrystallized from Et2O
  9. customdried in vacuo (0.1 mm) at 85° C.
  10. customto provide pure product, mp of 106°-109° C.

Sources & evidence

ORD record
ord-8d9942cd3bcb4255815500133b95c726
Source dataset
uspto-grants-1999_03
Patent number
US05880121

Reaction notes

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