4-(3-Pyridinecarbonylamino)-1-piperidinecarboxylate → N-(piperidin-4-yl)pyridine-3-carboxamide

HRID 1899894Notes

Reaction equation

HRID 1899894 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13](C([O-])=O)[CH2:12][CH2:11]2)=[O:8])[CH:2]=1>Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[O:8])[CH:2]=1

Participants

3

Reactant 1

HCID 214716504-(3-Pyridinecarbonylamino)-1-piperidinecarboxylate

Product 1

HCID 16787823N-(piperidin-4-yl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1.2 g of the ethylene ketal of 4-(3-pyridinecarbonylamino)-1-piperidinecarboxylate and 20 mL of 6N HCl was heated under reflux for 6 h. The mixture was cooled, extracted with 20 mL of dichloromethane, then basified with 6N NaOH and extracted with 3×50 mL of chloroform. The combined chloroform extracts were dried over MgSO4 and concentrated under reduced pressure. Drying under vacuum gave 0.6 g of 4-(3-pyridinecarbonylamino)piperidine as an oil: 1H NMR (400 MHz, CDCl3) 8.96 (d, J=2 Hz, 1H), 8.72 (m, 1H), 8.10 (m, 1H), 7.40 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with 20 mL of dichloromethane
  5. extractionextracted with 3×50 mL of chloroform
  6. dry with materialThe combined chloroform extracts were dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customDrying under vacuum

Sources & evidence

ORD record
ord-89f718e3c52a40fe854a66966e3758c4
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

Loading…