Potassium Carbonate → HCID 14405997, compound

HRID 1651529Notes

Reaction equation

HRID 1651529 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:6]=2[CH:22]=1.[CH3:23][N:24](CCI)[C:25](C1C=CC=CC=1)(C1C=CC=CC=1)[C:26]1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[C:16]3[CH2:17][CH2:18][N:19]([CH2:26][CH2:25][NH:24][CH3:23])[CH2:20][CH2:21]3)[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14405995HCID 14405995, compoundHCID 14405996HCID 14405996, compound

Product 1

HCID 14405997HCID 14405997, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 4-(10,11-dihydro-3-fluoro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine (5 g; 0.017 mol) and 2-[N-methyl-N-(triphenylmethyl)amino]ethyl iodide (7.3 g; 0.017 mol) in 30 ml of methyl isobutyl ketone (MiBk) is heated to the refluxing temperature. Potassium carbonate (4.7 g; 0.034 mol) is added in a single portion at this temperature, and the mixture is then heated to the refluxing temperature under an argon atmosphere for 10 h. The mixture is cooled, filtered and evaporated to dryness. The residual oil is then taken up with methylene chloride and the mixture is washed with water and with saline, dried over magnesium sulphate and then evaporated to dryness. 100 ml of 1N hydrochloric acid are added to the oil obtained, and the mixture is then stirred for 5 hours at room temperature. The tritylmethanol is separated off by filtration, the mother liquors are neutralized with 2N aqueous sodium hydroxide, the product is extracted using methylene chloride and the extract is dried over magnesium sulphate and evaporated. The oil obtained is used without further purification in the following stage.

Workup

  1. temperatureis heated to the refluxing temperature
  2. temperaturethe mixture is then heated to the refluxing temperature under an argon atmosphere for 10 h
  3. temperatureThe mixture is cooled
  4. filtrationfiltered
  5. customevaporated to dryness
  6. washthe mixture is washed with water and with saline
  7. dry with materialdried over magnesium sulphate
  8. customevaporated to dryness
  9. addition100 ml of 1N hydrochloric acid are added to the oil
  10. customobtained
  11. customThe tritylmethanol is separated off by filtration
  12. extractionthe product is extracted
  13. dry with materialthe extract is dried over magnesium sulphate
  14. customevaporated
  15. customThe oil obtained
  16. customis used without further purification in the following stage

Sources & evidence

ORD record
ord-2b1ac7512abe4e8dbcb8a770dbf2b590
Source dataset
uspto-grants-1990_05
Patent number
US04929621

Reaction notes

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