Guanidine → HCID 178432057, compound

HRID 1384291Notes

Reaction equation

HRID 1384291 reaction equation
[NH2:1][C:2]([NH2:4])=[NH:3].[CH3:5][C:6]1[N:11]=[C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:9]2=[CH:8][C:7]=1[C:17](OCC)=[O:18]>CC(O)C>[CH3:5][C:6]1[N:11]=[C:10]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:9]2=[CH:8][C:7]=1[C:17]([NH:3][C:2]([NH2:4])=[NH:1])=[O:18]

Participants

4

Reactant 2

HCID 3520GuanidineHCID 21186750HCID 21186750, compound

Product 1

HCID 178432057HCID 178432057, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In an atmosphere of argon, metallic sodium (325.2 mg, 0.014 g atom) was dissolved in anhydrous methanol (20.0 ml) at room temperature, and the solution was mixed with guanidine hydrochloride (1.35 g, 14.1 mmol) at 0° C. After 1 hour of stirring at room temperature, the thus precipitated sodium chloride was removed by filtration using a glass filter and the resulting filtrate was evaporated under reduced pressure to obtain free guanidine. Guanidine and ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (500.0 mg, 2.02 mmol) were suspended in 2-propanol (12.0 ml) and heated under reflux for 18 hours. After cooling, the solvent was evaporated under reduced pressure, and the resulting residue was mixed with water and extracted with ethyl acetate. The thus obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure and then the thus formed crystals were washed with ether to obtain the title compound (165.1 mg, 31.2%) as white powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. additionthe resulting residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washthe thus formed crystals were washed with ether

Sources & evidence

ORD record
ord-4f2725909eaf4aeb80b659231a921b11
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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