Sodium Hydroxide → HCID 22678352, compound

HRID 1837756Notes

Reaction equation

HRID 1837756 reaction equation
[CH2:1]([N:4]([CH2:24][C:25]#[CH:26])[C:5](=[O:23])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C:15]1[C:16]([O:21]C)=[N:17][CH:18]=[CH:19][CH:20]=1)[C:2]#[CH:3].S(Cl)(Cl)=O.[OH-].[Na+]>C(O)C>[CH2:1]([N:4]([CH2:24][C:25]#[CH:26])[C:5](=[O:23])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[CH2:14][C:15]1[C:16](=[O:21])[NH:17][CH:18]=[CH:19][CH:20]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 22678281HCID 22678281, compound

Product 1

HCID 22678352HCID 22678352, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

300 mg of N1,N1-di(2-propynyl)-3-[1-[(2-methoxy-3-pyridyl)methyl]-2-piperidyl]propanamide obtained in Example 176, 0.4 ml of thionyl chloride and 5 ml of ethanol were stirred under reflux for 1 hour, and then the mixture was left overnight. An aqueous dilute sodium hydroxide was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over sodium sulfate. The sodium sulfate was removed, and the solvent was evaporated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1, subsequently ethyl acetate:methanol=9:1), to give 300 mg of a yellow oil.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. customThe sodium sulfate was removed
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography (hexane

Sources & evidence

ORD record
ord-476d9bc7e9fc4ae683dd238364e0acdd
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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