2'-Nitroacetophenone → HCID 58504068, compound

HRID 2407776Notes

Reaction equation

HRID 2407776 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])[CH3:11])([O-:3])=[O:2].[CH:13]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=O>O1CCCC1.[O-]CC.[Na+].C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:12])/[CH:11]=[CH:13]\[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 113462'-NitroacetophenoneHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 58504068HCID 58504068, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 2723922Sodium ethoxideCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Nitrophenyl)ethanone (1.04 g) and tert-butyl 4-formylpiperidine-1-carboxylate (1.47 g) were suspended in dry tetrahydrofuran (20 mL) and 20 drops of sodium ethoxide in ethanol (21% by weight) was added. The reaction mixture was stirred at room temperature for 18 hours and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography (eluant: 15% ethyl acetate/hexane) to furnish the title compound (1.30 g) with the following physical properties.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto afford the crude material, which
  3. customwas purified by flash column chromatography (eluant: 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dffdecba8b4a4dcdb716826fdea150ae
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…