Potassium Carbonate → HCID 10895908, compound

HRID 1004081Notes

Reaction equation

HRID 1004081 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][CH2:17][CH2:18]O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O.Br.[C:26]1([C:32]2([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.C(N(CC)CC)C.CC(=O)CC.O>[CH2:41]([O:40][C:38]([C:32]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:33][CH2:34][N:35]([CH2:18][CH2:17][CH:16]=[C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]2=3)[CH2:36][CH2:37]1)=[O:39])[CH3:42]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1113956014341-94-7HCID 18794171227470-64-6

Product 1

HCID 10895908HCID 10895908, compoundYield 81.3%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propanol (3.5 g, 14 mmol) in benzene (50 ml), triethylamine (4 ml) and methanesulfonyl chloride (2.0 g, 17.4 mmol) were added and the reaction mixture was stirred at room temperature for 6 h. Water was added and the phases were separated. The organic phase was dried (MgSO4) and solvent was evaporated in vacuo to give a residue which was dissolved in 2-butanone (50 ml). Ethyl 4-phenyl-4-piperidine-carboxylate hydrobromide (4.4 g, 14 mmol) and potassium carbonate (4.4 g, 32 mmol) were added and the mixture was heated at reflux temperature for 24 h. The mixture was filtered and the solvent evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (50 g) using ethyl acetate as eluent to give 5.3 g of 1-(3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)-4-phenyl-4-piperidinecarboxylic acid ethyl ester as an oil.

Workup

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried (MgSO4) and solvent
  3. customwas evaporated in vacuo
  4. customto give a residue which
  5. temperaturethe mixture was heated
  6. temperatureat reflux temperature for 24 h
  7. filtrationThe mixture was filtered
  8. customthe solvent evaporated in vacuo
  9. customThe oily residue was purified by column chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-3551719cee6b4d7abe9ec480c31c468a
Source dataset
uspto-grants-2000_04
Patent number
US06048856

Reaction notes

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