Maltol → HCID 12997616, compound

HRID 585415Notes

Reaction equation

HRID 585415 reaction equation
[CH3:1][C:2]1O[CH:7]=[CH:6][C:4](=[O:5])[C:3]=1[OH:9].[NH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>O>[N:11]1([N:10]2[CH:7]=[CH:6][C:4](=[O:5])[C:3]([OH:9])=[C:2]2[CH3:1])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8369MaltolHCID 166581-Aminopiperidine

Product 1

HCID 12997616HCID 12997616, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Maltol (3.6 g, 30 mmol) and 1-aminopiperidine (4.5 g, 45 mmol) were suspended in 100 mL of water. The mixture was heated to reflux for 2 days. The mixture was cooled to room temperature, and the solvent was removed under vacuum to give a dark brown liquid. The residue was allowed to stand overnight, a solid was formed. The solid was collected by filtration and was then recrystallized in water to give brownish microcrystals. The product was collected by filtration, washed with water, and dried under vacuum overnight. The yield was 0.64 g (˜10.2%). LC-MS: M/z=209.3 for [C11H16N2O2]+. 1H NMR (600 MHz, in CD3OD, chemical shift in ppm relative to TMS): 1.34 (m, 1H, CH2); 1.81 (m, 5H, CH2); 2.40 (s, 3H, CH3); 3.00 (m, 4H, CH2); 6.43 (d, 1H, JHH=7.5 mHz, CH2/pyridinone); and 7.99 (d, 1H, JHH=7.5 mHz, CH/pyridinone).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 days
  3. customthe solvent was removed under vacuum
  4. customto give a dark brown liquid
  5. customa solid was formed
  6. filtrationThe solid was collected by filtration
  7. customwas then recrystallized in water
  8. customto give brownish microcrystals
  9. filtrationThe product was collected by filtration
  10. washwashed with water
  11. customdried under vacuum overnight

Sources & evidence

ORD record
ord-e309a930697b407b853220bbb62728d9
Source dataset
uspto-grants-2005_08
Patent number
US06932960B2

Reaction notes

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