Triethylamine → t-butyl 4-(5H-dibenzo[a,d][7]annulen-5-yl)-1-piperazine carboxylate

HRID 2374850Notes

Reaction equation

HRID 2374850 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6](O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N:28]1([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>C1C=CC=CC=1.N1C=CC=CC=1>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([N:31]3[CH2:30][CH2:29][N:28]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:33][CH2:32]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 82577DibenzosuberenolHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 68420841t-butyl 4-(5H-dibenzo[a,d][7]annulen-5-yl)-1-piperazine carboxylate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

750 mg (3.60 mmol) of the compound obtained in step 1 described above was dissolved in 8 ml of benzene. 0.02 ml of pyridine was added to the obtained solution, and 3.5 ml (48.2 mmol) of thionyl chloride was added to the obtained mixture under cooling with ice. After stirring the reaction mixture at 0° C. for 1 hour and then at room temperature for 2 hours, the solvent was evaporated under reduced pressure. 10 ml of tetrahydrofuran was added to the residue. 2.5 ml (18 mmol) of triethylamine and 805 mg (4.32 mmol) of t-butyl piperazinecarboxylate were added to reaction mixture under cooling with ice. The temperature of the mixture was slowly elevated to room temperature, and it was stirred overnight. The solvent was evaporated under reduced pressure. Dichloromethane was added to the residue. After washing with water and saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduce pressure, and the residue was purified by the basic silica gel chromatography (hexane:dichloromethane=9:1) to obtain the title compound.

Workup

  1. additionwas added to the obtained mixture
  2. temperatureunder cooling with ice
  3. waitat room temperature for 2 hours
  4. customthe solvent was evaporated under reduced pressure
  5. addition10 ml of tetrahydrofuran was added to the residue
  6. temperatureunder cooling with ice
  7. customwas slowly elevated to room temperature
  8. stirringit was stirred overnight
  9. customThe solvent was evaporated under reduced pressure
  10. additionDichloromethane was added to the residue
  11. washAfter washing with water and saturated aqueous sodium chloride solution
  12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated
  14. customthe residue was purified by the basic silica gel chromatography (hexane:dichloromethane=9:1)

Sources & evidence

ORD record
ord-34810954965749018def84f0313141ea
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

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