rac-1-[1-(3-Nitro-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide → rac-1-[1-(3-Amino-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide

HRID 1486696Notes

Reaction equation

HRID 1486696 reaction equation
[CH:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=3)[CH3:17])[CH2:12][CH2:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([NH:7][C:8]([CH:10]2[CH2:11][CH2:12][N:13]([CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=3)[CH3:17])[CH2:14][CH2:15]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 131736797rac-1-[1-(3-Nitro-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide

Product 1

HCID 131736798rac-1-[1-(3-Amino-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamideYield 102.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of rac-1-[1-(3-nitro-phenyl)-ethyl]-piperidine-4-carboxylic acid cyclohexylamide (375 mg, 1.04 mmol) in MeOH (15 mL) is treated with anhydrous stannous chloride (908 mg, 4.7 mmol). The mixture is heated at reflux overnight. The mixture is let to cool to RT and MeOH is evaporated under reduced pressure. Water (25 mL) is added to the residue, followed by saturated NaHCO3 solution (25 mL). The mixture is extracted twice with DCM (25 mL), the organic phases are washed with water (25 mL), brine (25 mL) and dried over MgSO4. The crude product (0.35 g, 99%) is isolated after evaporation under reduced pressure as a colorless oil: LC-MS A: tR=0.51 min; [M+H]+=330.31.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. customMeOH is evaporated under reduced pressure
  4. additionWater (25 mL) is added to the residue
  5. extractionThe mixture is extracted twice with DCM (25 mL)
  6. washthe organic phases are washed with water (25 mL), brine (25 mL)
  7. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-2f1d282e40674105bd9a80e7aa2517c9
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

Loading…