Guanidine Hydrochloride → HCID 69221023, compound

HRID 971216Notes

Reaction equation

HRID 971216 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.Cl.[NH2:22][C:23]([NH2:25])=[NH:24].C[O-].[Na+]>CO>[NH2:24][C:23]1[N:25]=[C:11]2[CH2:10][N:9]([CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:14][CH2:13][CH:12]2[C:15](=[O:17])[N:22]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 69221023HCID 69221023, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride (2.98 g, 10 mmol) and guanidine hydrochloride (1.15 g, 12 mmol) in a solution of sodium methoxide in methanol (11.5 mL, 25% wt) was stirred at 100° C. in a sealed tube overnight before solvent was removed in vacuo. Residue was dissolved in water (10 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 product was obtained as a light yellow powder (2.45 g).

Workup

  1. customwas removed in vacuo
  2. dissolutionResidue was dissolved in water (10 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-824d4f0947b449d69406c2412cec27b7
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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