Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride → HCID 69222805, compound

HRID 971204Notes

Reaction equation

HRID 971204 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=O)[C:11](=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:21]1[CH2:26][CH2:25][N:24]([CH2:27][CH:28]([NH2:30])[NH2:29])[CH2:23][CH2:22]1>C[O-].[Na+].CO>[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]2[C:11](=[N:30][C:28]([CH2:27][N:24]3[CH2:25][CH2:26][O:21][CH2:22][CH2:23]3)=[N:29][C:15]2=[O:17])[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 55289212HCID 55289212, compound

Product 1

HCID 69222805HCID 69222805, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl N-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (2.98 g, 10 mmol) and 2-Morpholinoethane-1,1-diamine (˜20 mmol) were dissolved in a solution of sodium methoxide in methanol (12 mL, 25% wt) and stirred at 100° C. in a sealed tube for 4 h. Solvent was removed in vacuo, residue was dissolved in water (100 mL) and was extracted by CHCl3 and i-PrOH (3:1, 5×80 mL), dried over sodium sulfate. Solvent was removed in vacuo, and the remaining brown solid residue was used directly in the next step.

Workup

  1. customSolvent was removed in vacuo, residue
  2. dissolutionwas dissolved in water (100 mL)
  3. extractionwas extracted by CHCl3 and i-PrOH (3:1, 5×80 mL)
  4. dry with materialdried over sodium sulfate
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-68d1775f5cb643bb890210002848a8c9
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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