Dimethylformamide → HCID 10480256, compound

HRID 1587011Notes

Reaction equation

HRID 1587011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([CH3:21])[NH:14][C:13]([CH3:22])=[C:12]2[C:23]([O:25][CH3:26])=[O:24])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CN(C)C=O.[C:32]1([CH2:38][CH2:39][CH2:40]Br)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[C:12]([C:23]([O:25][CH3:26])=[O:24])=[C:13]([CH3:22])[N:14]([CH2:40][CH2:39][CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:15]([CH3:21])=[C:16]2[C:17]([O:19][CH3:20])=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12503(3-Bromopropyl)benzeneHCID 982605HCID 982605, compound

Product 1

HCID 10480256HCID 10480256, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

60% Sodium hydride (0.26 g) was washed with several milliliters of anhydrous n-hexane in an argon gas atmosphere, and 10 ml dimethylformamide was added. To the resulting mixture, was added dropwise 20 ml of a dimethylformamide solution containing 2 g (5.5 mmol) dimethyl 1,4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate with stirring. The mixture was heated at 90° C. for one hour, 20 ml of a dimethylformamide solution of 3-phenylpropyl bromide was then added, and heating at 90° C. was continued for one hour. After cooling the mixture to room temperature, 20 ml diethyl ether was added, the resulting mixture was washed with water, and the solvent was distilled off under reduced pressure. The crude product thus obtained was purified by column chromatography (SiO2 /n-hexane-ethyl acetate 2:1), affording 0.8 g (30%) of the pure product. M.P.: 97°-98° C.

Workup

  1. wash60% Sodium hydride (0.26 g) was washed with several milliliters of anhydrous n-hexane in an argon gas atmosphere, and 10 ml dimethylformamide
  2. additionwas added
  3. additionTo the resulting mixture, was added dropwise 20 ml of a dimethylformamide solution
  4. temperatureheating at 90° C.
  5. temperatureAfter cooling the mixture to room temperature
  6. washthe resulting mixture was washed with water
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe crude product thus obtained
  9. customwas purified by column chromatography (SiO2 /n-hexane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-b07082051f7f42a3b4f946b3fa55d81b
Source dataset
uspto-grants-1993_06
Patent number
US05216172

Reaction notes

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