Ethyl 4-piperidinecarboxylate → Ethyl 1-(2-cyano-4-nitrophenyl)piperidine-4-carboxylate

HRID 1744506Notes

Reaction equation

HRID 1744506 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH:13]1[CH2:23][CH2:22][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14]1>[N+]([O-])([O-])=O.[Ag+]>[N+:10]([C:7]1[CH:8]=[CH:9][C:2]([N:13]2[CH2:23][CH2:22][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14]2)=[C:3]([C:4]#[N:5])[CH:6]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 9280152Ethyl 1-(2-cyano-4-nitrophenyl)piperidine-4-carboxylateYield 102.9%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

2-Chloro-5-nitrobenzonitrile (10 g), ethyl isonipecotate (60 g) and silver nitrate (11.1 g) were stirred at 120° C. for 3 h. The reaction mixture was cooled to room temperature and the solid was filtered off. To the filtrate was added dilute hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from hydrous diisopropyl ether to give ethyl 1-(4-nitro-2-cyanophenyl)piperidin-4-ylcarboxylate (17.1 g).

Workup

  1. filtrationthe solid was filtered off
  2. additionTo the filtrate was added dilute hydrochloric acid
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the residue
  8. customcrystallization
  9. customThe crystals were recrystallized from hydrous diisopropyl ether

Sources & evidence

ORD record
ord-447d1d4c46bb4480b37901bf0fe6c11c
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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