4-Piperidinecarboxamide → HCID 45275244, compound

HRID 1622352Notes

Reaction equation

HRID 1622352 reaction equation
Cl.Cl[C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[CH:5][C:4]=1[CH3:10].N1[CH2:19][CH2:18][CH:14]([C:15]([NH2:17])=[O:16])[CH2:13][CH2:12]1.[C:20](=O)([O-])O.[Na+]>O>[CH3:10][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH3:9])[C:3]=1[CH:20]1[CH2:19][CH2:18][CH:14]([C:15]([NH2:17])=[O:16])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 516892Sodium BicarbonateHCID 16090642HCID 16090642, compound

Product 1

HCID 45275244HCID 45275244, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-chloro-3,5-dimethylpyridine hydrochloride (0.10 g, 0.56 mmol) and isonipecotamide (0.22 mg, 1.7 mmol) in water (1.5 mL) was heated at 175° C. for 60 min, in a microwave reactor. The mixture was poured into a saturated solution of sodium hydrogen carbonate (20 mL), extracted with EtOAc (2×20 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 95:5) to furnish the title compound as a white solid (5 mg, 4%), m/z 234 (100%, [M+H]+); m/z (ESI) C13H20N3O requires 234.1601 found [M+H]+ 234.1600.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 95:5)

Sources & evidence

ORD record
ord-8a4f55bbc36b4224b28906c8a5e23d00
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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