Hydrochloric Acid → Methyl cis-5-aminopiperidine-3-carboxylate dihydrochloride

HRID 383789Notes

Reaction equation

HRID 383789 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1.[ClH:12]>CO>[ClH:12].[ClH:12].[NH2:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1514432Methyl 5-aminopyridine-3-carboxylate

Product 1

HCID 66659965Methyl cis-5-aminopiperidine-3-carboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of methyl 5-aminopyridine-3-carboxylate (700.0 mg) in MeOH (20 ml) was added 2 M aqueous solution of HCl (7 ml). And the mixture was hydrogenated (ca. 4 atm) for 1 day in a Parr low-pressure hydrogenation apparatus with a 5 wt. % Rh on Al2O3 catalyst (451.9 mg) at 80° C. Rh on Al2O3 catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was solidified from the mixed solvent of CHCl3 and MeOH to give methyl cis-5-aminopiperidine-3-carboxylate dihydrochloride as a cream-colored solid.

Workup

  1. customfor 1 day
  2. customat 80° C
  3. filtrationRh on Al2O3 catalyst was filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-317c56eec4e241cf807c8ef80bd53fe9
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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