Ethanol → HCID 18357280, compound
Reaction equation
[CH:1]([N:4]([CH:17]([CH3:19])[CH3:18])[CH2:5][CH2:6][CH:7]([C:14](=[O:16])N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[N+]([O-])(O)=O.[CH2:24]([OH:26])[CH3:25]>>[CH:1]([N:4]([CH:17]([CH3:19])[CH3:18])[CH2:5][CH2:6][CH:7]([C:14]([O:26][CH2:24][CH3:25])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2]Participants
Procedure
N,N-Diisopropyl-3-carbamyl-3-phenylpropanamine (26.5 g 0.100 mol) was added into aqueous ethanol (90%, 300 mL) containing conc. HNO3 (13.3 g, 0.21 mol) and refluxed for five days. Most of the solvent was evaporated under reduced pressure and the residue was mixed with water/diethyl ether. The organic phase was washed once with water. The combined aqueous phases were made alkaline (11 M NaOH) and extracted twice with diethyl ether. The combined organic phases were then dried (Na2SO4) and the solvent evaporated. The crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3), to afford the title compound as a colourless liquid, 20.1 g (68.7%): 1H NMR (CDCl3) δ0.96 (m, 12H), 1.21 (t, 3H), 1.81 (m, 1H), 2.22 (m, 1H), 2.40 (t, 2H), 3.66 (dd, 1H), 4.12 (m, 2H), 7.20-7.32 (m, 5H).
Workup
- temperaturerefluxed for five days
- customMost of the solvent was evaporated under reduced pressure
- additionthe residue was mixed with water/diethyl ether
- washThe organic phase was washed once with water
- extractionextracted twice with diethyl ether
- dry with materialThe combined organic phases were then dried (Na2SO4)
- customthe solvent evaporated
- customThe crude product was chromatographed on silica (petroleum ether-triethylamine, 97/3)
Sources & evidence
- ORD record
- ord-a69bec15aa0049168b6911e26317b9cb
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313132B1
Reaction notes
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