2-Pyridinecarboxaldehyde → HCID 17972785, compound

HRID 1685998Notes

Reaction equation

HRID 1685998 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:7])=[O:4].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=O.[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C(O)C(C)C>[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][N:21]1[CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH:8]([C:9]([O:11][CH3:12])=[O:10])[C:6](=[O:7])[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH:19]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 195092-PyridinemethanamineHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 17972785HCID 17972785, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
9 °C

Procedure

1 st stage: 44.89 g of dimethyl acetonedicarboxylate (97%; 0.25 mol) were initially charged in 125 ml of isobutanol. The mixture was cooled to 9° C. At this temperature, first 53.55 g of pyridine-2-aldehyde (0.5 mol) were added dropwise. Subsequently, 27.03 g of aminomethylpyridine (0.25 mol) were added dropwise at such a rate that the temperature could be maintained. The mixture was then heated to approximately 50° C., and approx. 65 ml of isobutanol-water mixture were distilled off under reduced pressure at internal temperature approx. 50° C., in the course of which approx. 65 ml of fresh isobutanol were simultaneously metered in. After the distillation had ended, the mixture was vented and cooled to 20° C. The product was filtered off, washed repeatedly with isobutanol and dried at 50° C. under reduced pressure. 100.6 g (87.4%) of 1-(pyridin-2-ylmethyl)-2,6-dipyridyl-3,5-di(methoxycarbonyl)-4-piperidone were obtained as a beige-white powder.

Workup

  1. temperaturecould be maintained
  2. temperatureThe mixture was then heated to approximately 50° C.
  3. distillationapprox. 65 ml of isobutanol-water mixture were distilled off under reduced pressure at internal temperature approx. 50° C., in the course of which approx. 65 ml of fresh isobutanol
  4. distillationAfter the distillation
  5. temperaturecooled to 20° C
  6. filtrationThe product was filtered off
  7. washwashed repeatedly with isobutanol
  8. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-785226b65aad4fd0af9c2c70875d7293
Source dataset
uspto-grants-2012_04
Patent number
US08148530B2

Reaction notes

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