Piperidine-1-carboxamidine → 2-(6-Oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

HRID 1399730Notes

Reaction equation

HRID 1399730 reaction equation
[N:1]1([C:7](=[NH:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]([CH:18]([CH:24]([CH2:30][CH2:31][CH3:32])[C:25]([O:27]CC)=[O:26])[C:19](OCC)=[O:20])(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[O-].[Na+]>CO>[O:20]=[C:19]1[NH:8][C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:9][C:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:18]1[CH:24]([CH2:30][CH2:31][CH3:32])[C:25]([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 205051Piperidine-1-carboxamidineHCID 10942334Sodium MethoxideHCID 66955320Diethyl 2-benzoyl-3-propylsuccinate

Product 1

HCID 1363461692-(6-Oxo-4-phenyl-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of piperidine-1-carboximidamide (dimer complexated with H2SO4) (0.6 g; 4.71 mmol) and diethyl 2-benzoyl-3-propylsuccinate (1.51 g; 4.71 mmol) in methanol (5 mL) was slowly added a solution of sodium methoxide in methanol (25% w:w) (2.16 mL; 9.43 mmol) and the reaction was heated to reflux for 21 h. The volatiles were removed under reduced pressure and the crude residue was used as such in the next reaction.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 21 h
  3. customThe volatiles were removed under reduced pressure
  4. customsuch in the next reaction

Sources & evidence

ORD record
ord-0ff40907276142138d4dc7b53ed5a47b
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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