Hydrochloric Acid → HCID 22678281, compound

HRID 1837752Notes

Reaction equation

HRID 1837752 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH2:16][CH2:17][C:18]([O:20]CC)=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[Na+].Cl>CO>[CH2:3]([N:4]([CH2:5][C:6]#[CH:7])[C:18](=[O:20])[CH2:17][CH2:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][N:10]1[CH2:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1)[C:8]#[CH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22678737HCID 22678737, compound

Product 1

HCID 22678281HCID 22678281, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

500 mg of ethyl 3-[1-[(2-methoxy-3-pyridyl)methyl]-2-piperidyl]propanoate, 2 ml of a 2N aqueous sodium hydroxide and 2 ml of methanol were stirred at 60° C. for 2 hours. After cooling to room temperature, 4 ml of a 1N aqueous hydrochloric acid was added thereto and the solvent was evaporated. Ethanol was added to the residue, the insoluble matters were filtered off and the solvent was evaporated. The resulting oil (500 mg), 170 mg of dipropargylamine, 450 mg of WSC and 240 mg of HOBt were dissolved in DMF, followed by stirring under room temperature for 3 hours. 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=2:1to 1:1, subsequently ethyl acetate), to give 300 mg of an oil.

Workup

  1. customthe solvent was evaporated
  2. additionEthanol was added to the residue
  3. filtrationthe insoluble matters were filtered off
  4. customthe solvent was evaporated
  5. dissolutionThe resulting oil (500 mg), 170 mg of dipropargylamine, 450 mg of WSC and 240 mg of HOBt were dissolved in DMF
  6. additionWater was added
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried over sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-658ce55162ba498a8c9abc2f543cf5e4
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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