Ethyl Acetate → 1-(4-Amino-phenyl)-piperidine-4-carboxylic acid ethyl ester

HRID 718658Notes

Reaction equation

HRID 718658 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-].CCOC(C)=O>CO.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 2796870Ethyl 1-(4-nitrophenyl)piperidine-4-carboxylate

Product 1

HCID 27641811-(4-Amino-phenyl)-piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of compound 54a (15 g, 51 mmol) in MeOH (100 mL) was added saturated NH4Cl solution (100 mL) followed by Fe(s) (9.1 g, 160 mmol). The resulting mixture was stirred for 5 h at 80° C. and then 200 mL of EtOAc was added. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:5 v/v)) to obtain compound 54b as a black solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C14H20N2O2: 249.2 (M+H). Found 249.0.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:5 v/v))

Sources & evidence

ORD record
ord-50cded1897824598916380f1b8640c61
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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