Potassium Carbonate → HCID 11069527, compound

HRID 2226749Notes

Reaction equation

HRID 2226749 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](=[N:16][O:17][CH2:18][CH2:19]Br)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C(C(O)=O)O)O)(O)=O.[NH:37]1[CH2:42][CH2:41][CH2:40][C@@H:39]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:38]1>CC(CC(C)C)=O>[CH2:46]([O:45][C:43]([C@@H:39]1[CH2:40][CH2:41][CH2:42][N:37]([CH2:19][CH2:18][O:17][N: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)[CH2:38]1)=[O:44])[CH3:47]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2733695(R)-(-)-Ethyl Nipecotate TartrateHCID 18965305HCID 18965305, compound

Product 1

HCID 11069527HCID 11069527, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a solution of 2-(((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)amino)oxy)ethylbromide (1.4 g, 4.2 mmol) in methyl isobutylketone (40 ml) was added potassium carbonate (4.7 g, 34 mmol) and ethyl (R)-3-piperidinecarboxylate tartrate (2.6 g, 8.5 mmol) and the suspension was heated at reflux temperature for 3 days. The cooled reaction mixture was filtered and the solvent was evaporated from the filtrate in vacuo. The oily residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml). A 34% aqueous tartaric acid solution was added until pH 4. The phases were separated and the aqueous phase was extracted with ethyl acetate (25 ml). The combined organic phases were extracted with a 34% aqueous tartaric 1/2acid solution (2×5 ml) and the organic extracts were discarded. The acidic aqueous phases were combined, diluted three times with water and ethyl acetate (40 ml) was added. A 4 N sodium hydroxide solution was added until pH 7 and the phases were separated. The organic phase was washed with brine and dried over sodium sulphate. The solvent was evaporated in vacuo to give 1 g of (R)-N-(2-(((10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)amino)oxy)ethyl)-3-piperidinecarboxylic acid ethyl ester as an oil. TLC: rf=0.39 (SiO2 ; dichloromethane/methanol/acetic acid=20:2:1).

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux temperature for 3 days
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe solvent was evaporated from the filtrate in vacuo
  6. dissolutionThe oily residue was dissolved in a mixture of ethyl acetate (50 ml) and water (50 ml)
  7. additionA 34% aqueous tartaric acid solution was added until pH 4
  8. customThe phases were separated
  9. extractionthe aqueous phase was extracted with ethyl acetate (25 ml)
  10. extractionThe combined organic phases were extracted with a 34% aqueous tartaric 1/2acid solution (2×5 ml)
  11. additiondiluted three times with water and ethyl acetate (40 ml)
  12. additionwas added
  13. additionA 4 N sodium hydroxide solution was added until pH 7
  14. customthe phases were separated
  15. washThe organic phase was washed with brine
  16. dry with materialdried over sodium sulphate
  17. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8bdfbfb3f7194052808e1f200208ce3b
Source dataset
uspto-grants-1994_09
Patent number
US05348965

Reaction notes

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