Acetic Acid → 6-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

HRID 535343Notes

Reaction equation

HRID 535343 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18]CC)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O)(=O)C.[CH:25]([NH2:27])=[NH:26].C[O-].[Na+].C(O)(=O)C>CO.[OH-].[Na+]>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2[N:26]=[CH:25][NH:27][C:16](=[O:18])[C:11]=2[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 102623Ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Product 1

HCID 1355929356-benzyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (50.0 g, 0.168 mol), formamidine acetate (16.2 g, 0.201 mol), 4.37 M of sodium methoxide in methanol (190 mL) and methanol (200 mL, 5 mol) was heated to 85° C. for 16 hour in a 350 ml sealed reaction vessel. The mixture was allowed to cool and reduced in vacuo. The residue was dissolved in 1N NaOH (150 ml) and poured over ice. Glacial acetic acid was added to the mixture until the pH of the mixture was 7 and a tan solid precipitated out the solid was filtered, washed with water and cold ether, and dried on high vacuum to yield the title compound as a tan solid; (26.2 g, 61.4%).

Workup

  1. customsealed
  2. customreaction vessel
  3. temperatureto cool
  4. additionpoured over ice
  5. customa tan solid precipitated out the solid
  6. filtrationwas filtered
  7. washwashed with water and cold ether
  8. customdried on high vacuum

Sources & evidence

ORD record
ord-2fd67665d17644f8881f2e4abf84d66b
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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