1-Methylpiperazine → HCID 20491794, compound

HRID 434703Notes

Reaction equation

HRID 434703 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[CH:17]=[C:16](Br)[C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[O:23])[C:12]=2[CH:24]=1.BrC1C=CC2C(Br)=CC3C=CC=CC=3C(=O)C=2C=1.[CH3:43][N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>C(O)(C)(C)C>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:17]([N:47]3[CH2:48][CH2:49][N:44]([CH3:43])[CH2:45][CH2:46]3)=[CH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[C:13](=[O:23])[C:12]=2[CH:24]=1

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 20491798HCID 20491798, compoundHCID 20491800HCID 20491800, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20491794HCID 20491794, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (6.8 g., 0.06 mole) was added to a stirred slurry of 3,10-dibromo-5H-dibenzo[a,d]cyclohepten-5-one and 3,11-dibromo-5H-dibenzo[a,d]cyclohepten-5-one (18.2 g., 0.05 mole), 4-methylpiperazine (10 ml.), and dry tert-butyl alcohol (200 ml.) at room temperature and under nitrogen. The dark orange mixture was heated to refluxing for 2 hours and then stirred at room temperature overnight. The mixture was poured into approximately 800 ml. of ice and water and extracted with ether. The ether extract was washed with water, dried over anhydrous sodium sulfate, filtered, and evaporated. The mixture of 3-bromo-10-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-one and 3-bromo-11-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-one was obtained as a residual red-yellow gum; yield, 19.4 g. 100%.

Workup

  1. temperatureThe dark orange mixture was heated
  2. temperatureto refluxing for 2 hours
  3. additionThe mixture was poured into approximately 800 ml
  4. extractionof ice and water and extracted with ether
  5. extractionThe ether extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. additionThe mixture of 3-bromo-10-(4-methylpiperazinyl)-5H-dibenzo[a,d]cyclohepten-5-one

Sources & evidence

ORD record
ord-3cc26e6fded24a509ac8d415b8c5186e
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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