Benzene → HCID 54533726, compound

HRID 866595Notes

Reaction equation

HRID 866595 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]1[CH:24]=[CH:23][C:11]2[O:12][C:13]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:14]=3[C:15](=O)[CH2:16][C:10]=2[CH:9]=1.[CH2:25]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:29])[CH3:26].C(=O)(O)[O-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.O>[CH2:25]([O:27][C:28]([N:30]1[CH2:31][CH2:32][N:33]([C:15]2[C:14]3[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:13]=3[O:12][C:11]3[CH:23]=[CH:24][C:8]([CH3:7])=[CH:9][C:10]=3[CH:16]=2)[CH2:34][CH2:35]1)=[O:29])[CH3:26]

Participants

7

Reactant 4

HCID 241Benzene2×HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 516892Sodium BicarbonateHCID 22767888HCID 22767888, compound

Product 1

HCID 54533726HCID 54533726, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Procedure

A solution of 11.35 ml. of titanium (IV) chloride in 135 ml. of benzene is added dropwise with stirring and cooling at 20°-25° C. to a solution of 30 g. of 10,11-dihydro-2,8-dimethyl-dibenz[b,f]oxepin-10-one and 80 ml. of N-ethoxycarbonylpiperazine in 300 ml. of benzene. Then, the mixture is stirred for 4 hours at reflux and cooled. The cooled mixture is poured into a solution of 12 g. of sodium bicarbonate in 300 ml. of water. The precipitated titanium dioxide is removed by filtration and washed well with benzene. The filtrate is washed four additional times with water. The aqueous phases are extracted again with benzene. The combined benzene extracts are dried over sodium sulfate and evaporated in vacuo, and there is obtained 4-[2,8-dimethyl-dibenz[b,f]oxepin-10-yl]-1-piperazinecarboxylic acid ethyl ester as an oil.

Workup

  1. temperaturecooling at 20°-25° C. to a solution of 30 g
  2. stirringThen, the mixture is stirred for 4 hours
  3. temperatureat reflux
  4. temperaturecooled
  5. additionThe cooled mixture is poured into a solution of 12 g
  6. customThe precipitated titanium dioxide is removed by filtration
  7. washwashed well with benzene
  8. washThe filtrate is washed four additional times with water
  9. extractionThe aqueous phases are extracted again with benzene
  10. dry with materialThe combined benzene extracts are dried over sodium sulfate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-59393c5f01be469cae78bc8f4e418633
Source dataset
uspto-grants-1978_07
Patent number
US04100173

Reaction notes

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