Benzene → HCID 22767937, compound

HRID 437822Notes

Reaction equation

HRID 437822 reaction equation
C1C=CC=CC=1.[F:7][C:8]1[CH:23]=[CH:22][C:11]2[O:12][C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15](=O)[CH2:16][C:10]=2[CH:9]=1.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(=O)(O)[O-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O>[F:7][C:8]1[CH:23]=[CH:22][C:11]2[O:12][C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)=[CH:16][C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 241Benzene2×HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 22767907HCID 22767907, compound

Product 1

HCID 22767937HCID 22767937, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 6.44 g. of titanium (IV) chloride in 25 ml. of benzene is added dropwise over a period of 15 minutes with cooling to a solution of 9.12 g. of 2-fluoro-10,11-dihydro-dibenz[b,f]oxepin-10-one and 18 g. of 1-methyl-piperazine in 100 ml. of benzene in such a manner that the temperature does not exceed 25° C. The mixture is subsequently stirred for 4 hours at reflux. The resulting mixture is cooled and poured into a solution of 10 g. of sodium bicarbonate in 100 ml. of water. The precipiated titanium dioxide is removed by filtration and washed carefully with benzene and chloroform. The benzene solution and the chloroform solution are washed four times with water, combined, dried over sodium sulfate, evaporated in vacuo, and there is obtained crude, crystalline 1-[2-fluoro-dibenz[b,f]oxepin-10-yl]-4-methyl-piperazine.

Workup

  1. temperaturewith cooling to a solution of 9.12 g
  2. customdoes not exceed 25° C
  3. temperatureat reflux
  4. temperatureThe resulting mixture is cooled
  5. additionpoured into a solution of 10 g
  6. customThe precipiated titanium dioxide is removed by filtration
  7. washwashed carefully with benzene and chloroform
  8. washThe benzene solution and the chloroform solution are washed four times with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-30f96e07d4d44f54b229223c0345cfda
Source dataset
uspto-grants-1977_06
Patent number
US04032525

Reaction notes

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