4-[2-(3-NITROPHENOXY)ETHYL]MORPHOLINE synthesis
- Product Name:4-[2-(3-NITROPHENOXY)ETHYL]MORPHOLINE
- CAS Number:182618-90-2
- Molecular formula:C12H16N2O4
- Molecular Weight:252.27
89583-07-3
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Yield:182618-90-2 75%
Reaction Conditions:
with potassium carbonate in tetrahydrofuran at 20; for 6 h;
Steps:
2.3.2. Synthesis and characterization of 4-(2-(3-nitrophenoxy) ethyl) morpholine cpd.5
To a stirring solution of 3-nitrophenol (1 mmol) and 4-(2- bromoethyl) morpholine (1 mmol) in THF (10 ml) was added K 2 CO 3 (1.5 mmol) at room temperature. After stirring for 6 h at room temperature, the mixture was filtered and the filtrate was diluted by H 2 O (10 ml), and then extracted by CH 2 Cl 2 (10 ml ×3). The combined organic layer was washed by brine, dried over an- hydrous MgSO 4 , filtered, and concentrated. The residue was pu- rified over silica gel column (EtOAc: petroleum ether = 1: 2) to yield compound Cpd.5 . Yellow solid; yield: 75%; mp: 56-58 °C; IR (KBr, v, cm -1 ): 2928, 2855 (CH 2 ), 1526, 1346 (NO 2 ); 1 H NMR (500 M, CDCl 3 ) 7.83 (dd, J 1 = 8.2, J 2 = 2.1 Hz, 1H, Ar-H), 7.75 (t, J = 2.3 Hz, 1H, Ar-H), 7.42 (t, J = 8.2 Hz, 1H, Ar-H), 7.25-7.21 (m, 1H, Ar-H), 4.18 (t, J = 5.6 Hz, 2H, -O-CH 2 CH 2 -N), 3.75-3.73 (m, 4H, morpholine), 2.84 (t, J = 5.6 Hz, 2H, -O-CH 2 CH 2 -N), 2.59 (t, J = 4.7 Hz, 4H, morpholine); 13 C NMR (151 MHz, CDCl 3 ) 159.42, 149.38, 130.09, 121.89, 116.08, 109.03, 67.03, 66.71, 57.54, 54.25; HRMS (ESI) m/z calcd. for C 12 H 17 N 2 O 4 [ M + H ] + 253.1183, found 253.1183.
References:
Wang, Bo;Yang, Yang;Wang, Weixiao;Yu, Jiaoyang;Zhang, Fengwan;Wu, Shuo;Xu, Shijie;Du, Na;Qin, Xiaoyu;Song, Huijuan;Wu, Wenhao;Jiang, Bin;Liu, Mingliang;Wang, Apeng;Lv, Kai;Chen, Wei [Journal of Molecular Structure,2023,vol. 1273,art. no. 134284]
3240-94-6
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534-17-8
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182618-90-2
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