Water → HCID 22678450, compound

HRID 1837754Notes

Reaction equation

HRID 1837754 reaction equation
Cl.Cl.C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)C=CC=CC=1.CC(C)([O-])C.[K+].C[O:36][C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]2[CH2:50][CH:51]=O)=[CH:41][CH:40]=[CH:39][N:38]=1.O>CN(C=O)C>[O:36]=[C:37]1[C:42]([CH2:43][N:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH:45]2[CH2:50][CH2:51][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:41][CH:40]=[CH:39][NH:38]1

Participants

6

Reactant 4

HCID 962WaterHCID 22678440HCID 22678440, compoundHCID 22678470HCID 22678470, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22678450HCID 22678450, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In DMF was dissolved 2.1 g of triphenyl(2-pyridylmethyl)phosphonium dihydrochloride, followed by adding 1.4 g of potassium tert-butoxide thereto at room temperature under stirring. After 15 minutes, a solution of 1.25 g of 2-[1-[(2-methoxy-3-pyridyl)methyl]-2-piperidyl]acetaldehyde dissolved in DMF was added dropwise into the above-mentioned solution at room temperature under stirring, and the mixture was left overnight. Water was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1, subsequently ethyl acetate, and subsequently ethyl acetate:methanol=4:1). 760 mg of the resulting brown oil, 0.56 ml of thionyl chloride and 10 ml of ethanol were stirred under reflux for 30 minutes. The reaction solution was cooled to room temperature, a 2N aqueous sodium hydroxide was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1, subsequently ethyl acetate, and subsequently ethyl acetate:methanol=4:1). The resulting yellow oil (350 mg) was dissolved in 10 ml of ethanol, 100 mg of 10% palladium-carbon (water-containing product) was added thereto, and the mixture was catalytically hydrogenated at normal pressure under stirring for 1.5 hours. The catalyst was filtered off and the solvent was evaporated. The residue was purified by NH-silica gel chromatography (ethyl acetate, subsequently ethyl acetate:methanol=4:1), to give 310 mg of an oil.

Workup

  1. additionwas added dropwise into the above-mentioned solution at room temperature
  2. stirringunder stirring
  3. waitthe mixture was left overnight
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (hexane
  8. stirring760 mg of the resulting brown oil, 0.56 ml of thionyl chloride and 10 ml of ethanol were stirred
  9. temperatureunder reflux for 30 minutes
  10. temperatureThe reaction solution was cooled to room temperature
  11. additiona 2N aqueous sodium hydroxide was added
  12. extractionthe mixture was extracted with ethyl acetate
  13. dry with materialThe extract was dried over sodium sulfate
  14. customthe solvent was evaporated
  15. customThe residue was purified by silica gel column chromatography (hexane
  16. dissolutionThe resulting yellow oil (350 mg) was dissolved in 10 ml of ethanol
  17. addition100 mg of 10% palladium-carbon (water-containing product) was added
  18. stirringunder stirring for 1.5 hours
  19. filtrationThe catalyst was filtered off
  20. customthe solvent was evaporated
  21. customThe residue was purified by NH-silica gel chromatography (ethyl acetate, subsequently ethyl acetate

Sources & evidence

ORD record
ord-6b62d40443ab4776bd97632734e0aaa3
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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