Piperidine → 6-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione

HRID 496310Notes

Reaction equation

HRID 496310 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[N:4]([CH2:13][CH2:14][CH3:15])[C:3]1=[O:16].[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)[CH3:18].N1CCCCC1>C(O)C>[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1/[CH:22]=[CH:12]/[C:5]1[N:4]([CH2:13][CH2:14][CH3:15])[C:3](=[O:16])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=1[N+:9]([O-:11])=[O:10])[CH3:18]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11950Benzaldehyde, 2-ethoxy-HCID 223255723,6-dimethyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione

Product 1

HCID 223255706-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dioneYield 75.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,6-dimethyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione (6.25 g, 27.5 mmol), 2-ethoxybenzaldehyde (4.24 mL, 30.3 mmol), piperidine (2.83 mL, 28.6 mmol) and 3 Å molecular sieves (8.75 g) in ethanol (125 mL) was refluxed for 5 hours. The resulting suspension was filtered and the filtrate was evaporated under reduced pressure. The residue was triturated with isopropyl ether and the precipitate collected by filtration and dried under vacuum to yield 6-[(E)-2-(2-ethoxyphenyl)vinyl]-3-methyl-5-nitro-1-propyl-1H-pyrimidine-2,4-dione (7.42 g, 75%) as a yellow solid.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe resulting suspension was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated with isopropyl ether
  5. filtrationthe precipitate collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ded9ff69bbb7454797577c9f12b2c426
Source dataset
uspto-grants-2005_09
Patent number
US06943253B2

Reaction notes

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