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

HRID 226380Notes

Reaction equation

HRID 226380 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-08599cee364f432e84e10d4882b57e03
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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