4-(2-MORPHOLIN-4-YL-ETHYL)-ANILINE synthesis
- Product Name:4-(2-MORPHOLIN-4-YL-ETHYL)-ANILINE
- CAS Number:262368-47-8
- Molecular formula:C12H18N2O
- Molecular Weight:206.28
210158-20-6
262368-47-8
General procedure: 4-(4-nitrophenylethyl)morpholine (2 g, 8.46 mmol) was mixed with 500 mg of Pd/C catalyst in 100 mL of methanol and the reaction was stirred at 45 psi hydrogen pressure for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration to afford 4-(2-morpholin-4-ethyl)aniline (1.9 g, quantitative yield) as a white solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 6.99 (d, J=9Hz, 2H), 6.62 (d, J=9Hz, 2H), 3.73 (m, 4H), 3.60 (brs, 2H), 2.70-2.65 (m, 2H), 2.54-2.47 (m, 6H).
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Yield:-
Reaction Conditions:
Stage #1:2-(4-nitrophenyl)ethanol with iron(III) chloride in methanolHeating / reflux;
Stage #2: with hydrazine in methanol for 5 h;Product distribution / selectivity;Heating / reflux;
Steps:
d
The niro compound made in step c (150 g) was dissolved in MeOH (2L). FeCU (7.5 g) and activated carbon (15 g) were added and the reaction mixture was heated to reflux. Hydrazine hydrate (300 mL) was added slowly over 1 hour, and then the reaction was refluxed for 4 hours. The reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to a solid which was taken up in water (1 L) and cooled to 0 0C. The precipitated solids were collected by filtration and dried to give the desired product as an off white solid (125 g). IH NMR (300 MHz, DMSO-d6) δ ppm 6.87 (d, 2H, J = 8.3), 6.5 (d, 2H, J = 8.3), 4.84 (s, 2H), 3.59 (m, 4H), 2.56 (m, 2H), 2.41 (m, 6H)
References:
SMITHKLINE BEECHAM CORPORATION WO2007/18941, 2007, A2 Location in patent:Page/Page column 64
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