N,N-Diethyl-3-nitro-benzeneethanamine synthesis
- Product Name:N,N-Diethyl-3-nitro-benzeneethanamine
- CAS Number:932405-32-8
- Molecular formula:C12H18N2O2
- Molecular Weight:222.28
206874-43-3
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Yield:932405-32-8 75%
Reaction Conditions:
Stage #1: diethylaminewith potassium carbonate in acetonitrile; for 1 h;Heating / reflux;
Stage #2: 2-(3-nitrophenyl)ethyl methanesulfonate in acetonitrile; for 1 h;Heating / reflux;
Steps:
1.1k
N,N-diethyl-2-(3-nitrophenyl)ethanamine can be prepared by the following procedure. A mixture of diethyl amine (9.0 mmol) and K2CO3 (9.9 mmol) in ACN (50 mL) is refluxed for 1 h under nitrogen atmosphere. To the above mixture, a solution of 3-nitrophenethyl methanesulfonate (8.2 mmol) in ACN (10 mL) is added and the mixture is refluxed for 1 h. The solvent is removed and the residue is dissolved in DCM (100 mL). The organic layer is washed with water, dried over Na2SO4 and concentrated to afford a residue which is purified by silica gel column chromatography (EtOAc : hexane = 30 : 70) to afford N,N-diethyl-2-(3-niτrophenyl)ethanamine (75%). 1HNMR (400MHz, CDCl3) δ 8.04-8.10 (m, 2H), 7.51- 7.55 (d, J = 7.6 Hz, IH), 7.43 (t, J = 7.8 Hz, IH), 2.81-2.88 (m, 2H), 2.67-2.74 (m, 2H), 2.59 (q, J = 7.2 Hz,4H), 1.04 (t. J = 7.2 Hz, 6H). MS (m/z) (M+l)+ 223.2.
References:
WO2007/38669,2007,A2 Location in patent:Page/Page column 172
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