Ammonium formate → ethyl 6-[(3R)-3-piperidinylamino]nicotinate

HRID 2376065Notes

Reaction equation

HRID 2376065 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[C:25](Cl)=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68964359ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}-5-chloronicotinate

Product 1

HCID 68960377ethyl 6-[(3R)-3-piperidinylamino]nicotinateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-{[(3R)-1-benzyl-3-piperidinyl]amino}-5-chloronicotinate (6.75 g, 18.1 mmol) in ethanol (200 mL) were added ammonium formate (6.83 g, 108 mmol) and 10% Pd/C (20% w/w, 1.2 g) at ambient temperature and the mixture was heated to reflux with stirring for 8 hrs. After cooling, the catalyst in the reaction mixture was removed by filtration. The solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (NH, CHCl3 only-CHCl3:MeOH/50:1˜25:1) to give ethyl 6-[(3R)-3-piperidinylamino]nicotinate (4.5 g, 100%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe catalyst in the reaction mixture was removed by filtration
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (NH, CHCl3 only-CHCl3

Sources & evidence

ORD record
ord-8e40251b981742f4ba65b9d6367195bf
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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