p-Toluenesulfonic acid → N-cyclohexyl-C-(2-phenylethyl)nitrone

HRID 1242270Notes

Reaction equation

HRID 1242270 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]1([NH:17][OH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH:11]1([N+:17]([O-:18])=[CH:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7707BenzenepropanalHCID 72935Cyclohexylhydroxylamine

Product 1

HCID 562323N-cyclohexyl-C-(2-phenylethyl)nitroneYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3-phenylpropionaldehyde (5.0 g, 37.3 mmol, 1.0 equiv.) and CHCl3 (150 ml) was added N-cyclohexylhydroxylamine (4.30 g, 41.0 mmol, 1.1 equiv) and p-TsOH (few crystals) and the resulting mixture was refluxed under nitrogen for 22 h. Removal of the solvent an oil was obtained which was purified by flash chromatography (hexanes: EtOAc 1:1) to give N-cyclohexyl-C-(2-phenylethyl)nitrone (6.41 g, 74.4%) as a white solid, m.p. 97.2° C.: 1H NMR (CDCl3) δ 7.33–7.19 (m, 5H,), 6.69–6.65 (t, 1H, Ar—H), 3.67–3.56 (m, 1H), 2.91–2.78 (m, 4H), 1.97–1.63 (m, 7H), 1.37–1.10 (m, 3H).

Workup

  1. temperaturethe resulting mixture was refluxed under nitrogen for 22 h
  2. customRemoval of the solvent an oil
  3. customwas obtained which
  4. customwas purified by flash chromatography (hexanes: EtOAc 1:1)

Sources & evidence

ORD record
ord-d5d688b6ce4049eda78992f22ab60abf
Source dataset
uspto-grants-2006_10
Patent number
US07115666B2

Reaction notes

Loading…