Water → HCID 67179795, compound

HRID 1697891Notes

Reaction equation

HRID 1697891 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15]([O:17]C)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]([NH2:22])=[O:21].C[O-].[Na+].O>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]2[NH:19][C:20](=[O:21])[NH:22][C:15](=[O:17])[CH:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1176UreaHCID 107480Methyl 1-benzyl-4-oxo-3-piperidinecarboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 67179795HCID 67179795, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 1-benzyl-4-oxo-3-piperidinecarboxylate (20.194 g, 71.168 mmol) and urea (9.031 g, 150.4 mmol) were dissolved in methanol (150 mL). 4.63 M of sodium methoxide in methanol (46 mL) was added dropwise. Then the reaction was heated to reflux under nitrogen for 96 h. The reaction was cooled to 0° C. and filtered to give a white solid. This was stirred vigorously for 30 minutes with 50 ml water, then cooled to 0° C. and filtered to give 6-benzylhexahydropyrido[4,3-d]pyrimidine-2,4(1H,3H)-dione (ao) as a white solid (11.77 g, 45.7 mmol) which was dried under high vacuum overnight and then used without further purification: 1H NMR (D6-DMSO, 400 MHz) δ 7.47-7.07 (m, 5H), 3.56 (s, 2H), 2.96 (s, 2H), 2.51 (t, 4H), 2.27 (t, J=5.6, 2H).

Workup

  1. temperatureThen the reaction was heated
  2. temperatureto reflux under nitrogen for 96 h
  3. filtrationfiltered
  4. customto give a white solid
  5. temperaturecooled to 0° C.
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4dbb3249cc1b4cc3b742d3ac335406a4
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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