Hydrochloric Acid → HCID 19012835, compound

HRID 1729475Notes

Reaction equation

HRID 1729475 reaction equation
[NH2:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][C:5](=[O:14])[CH2:4][CH:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O>CO>[C:15]1([CH:3]2[CH:2]([NH:1][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=3[O:23][CH3:22])[CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:6][C:5](=[O:14])[CH2:4]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 19012812HCID 19012812, compound

Product 1

HCID 19012835HCID 19012835, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under a nitrogen atmosphere in a round bottom flask were placed 500 mg (1.9 mmol) of 5 -amino-4,6-diphenyl-2-oxopiperidine and 5 mL of methanol. To the system was added 1 g of 3 Å molecular sieves, and the pH of the mixture was adjusted to 4.5 using methanol saturated with hydrogen chloride. To this system was added 284 mg (2.1 mmol) of 2-methoxybenzaldehyde, and the mixture was stirred at room temperature overnight. The mixture was filtered through diatomaceous earth (Celite (trademark)), the filter cake was rinsed well with methanol and the filtrate was concentrated with a rotary evaporator. The residue was partitioned between saturated aqueous sodium bicarbonate and chloroform, the layers were separated and the aqueous phase was extracted with three portions of chloroform. The combined chloroform extracts were dried (sodium sulfate) and concentrated, and the residue was subjected to flash column chromatography (30 g of silica gel) using 3:97 methanol/chloroform as the eluant to obtain 115 mg of 4,6-diphenyl-5-(2-methoxybenzylamino)-2-oxopiperidine.

Workup

  1. customUnder a nitrogen atmosphere in a round bottom flask were placed
  2. additionTo the system was added 1 g of 3 Å molecular sieves
  3. filtrationThe mixture was filtered through diatomaceous earth (Celite (trademark))
  4. washthe filter cake was rinsed well with methanol
  5. concentrationthe filtrate was concentrated with a rotary evaporator
  6. customThe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with three portions of chloroform
  9. dry with materialThe combined chloroform extracts were dried (sodium sulfate)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3b7cda46f58d4002bd9802b196a83274
Source dataset
uspto-grants-1994_07
Patent number
US05332817

Reaction notes

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