Ammonia → 4-Amino-1-(pyridin-4-yl)piperidine-4-carboxylic acid methyl ester

HRID 412603Notes

Reaction equation

HRID 412603 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[C:14]([O-:17])(=[O:16])C.[NH4+:18].[C-:19]#N.[Na+].N.Cl>CO.Cl.CO.C(O)(=O)C>[CH3:19][O:17][C:14]([C:10]1([NH2:18])[CH2:11][CH2:12][N:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:8][CH2:9]1)=[O:16]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 517165Ammonium AcetateHCID 113327931-(Pyridin-4-yl)piperidin-4-one

Product 1

HCID 113453664-Amino-1-(pyridin-4-yl)piperidine-4-carboxylic acid methyl esterYield 56.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

To a solution of 1-(pyridin-4-yl)piperidin-4-one (1 g) in methanol solution were added ammonium acetate (880 mg), aqueous sodium cyanide solution (560 mg/5 ml), aqeuous ammonia (5 ml) and acetic acid (2 ml), and the mixture was tirred at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and aqueous ammonia (3 ml) was added and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated to give a residue. Hydrogen chloride was blown into a solution of the residue in 10% hydrogen chloride-methanol (25 ml) with ice-cooling and the solution was stood at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and to the obtained residue was added 2N-hydrochloric acid (25 ml). After stirring for 2 hr, the mixture was neutralized with sodium hydrogencarbonate and extracted with chloroform. The organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was dried under reduced pressure to give the title compound (760 mg).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionaqueous ammonia (3 ml) was added
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customto give a residue
  8. temperaturecooling
  9. waitthe solution was stood at room temperature for 12 hours
  10. customAfter completion of the reaction
  11. customthe solvent was evaporated and to the obtained residue
  12. additionwas added 2N-hydrochloric acid (25 ml)
  13. extractionextracted with chloroform
  14. washThe organic layer was washed successively with water and saturated brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was evaporated
  17. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-f62a5be87fbc49778244b5e5d419e30d
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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