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[ CAS No. 2689-39-6 ]

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Chemical Structure| 2689-39-6
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CAS No. :2689-39-6 MDL No. :MFCD03138381
Formula : C10H11FN2O3 Boiling Point : 380.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :226.20 g/mol Pubchem ID :-
Synonyms :

Safety of [ 2689-39-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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  • Upstream synthesis route of [ 2689-39-6 ]
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[ 2689-39-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 2689-39-6 ]
  • [ 93246-53-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol at 0℃; for 18 h; Description 2: 3-Fluoro-4- (4-morpholinyl) aniline 4-(2-Fluoro-4-nitrophenyl) morpholine D1 (42.6g, 0. 19mol) in ethanol (1.2L) was hydrogenated over 10percent Pd/C paste (4g) at STP for 18h. The resulting mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to afford the title product (36.9g, 100percent) as a colourless solid.'H NMR (CDCI3) 8 : 2.96 (4H, m), 3.55 (2H, br s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1H, m).
100% With hydrogen In ethanol at 20℃; for 18 h; 3-Fluoro-4- (4-morpholinyl) aniline 4-(2-Fluoro-4-nitrophenyl) morpholine D1 (42.6g, 0. 19mol) in ethanol (1.2L) was hydrogenated over 10percent Pd/C paste (4g) at NTP for 18h. The resulting mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to afford the title product (36.9g, 100percent) as a colourless solid. 1H NMR (CDCI3) b : 2.96 (4H, m), 3.55 (2H, br s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1 H, m).
100% With hydrogen In ethanol; ethyl acetate Method 22 3-Fluoro-4-morpholinoaniline; 1-Fluoro-2-morpholino-5-nitrobenzene (Method 21; 9g) in EtOH: EtOAc (50 : 50ml) was reduced with hydrogen over 10percent palladium/carbon (800mg). After filtering off the catalyst and washing with EtOH, evaporation of the filtrate gave the title compound as a brown solid (quantitative yield). NMR (CDC13) 2.96 (t, 4H), 3.55 (brs, 2H), 3. 84 (t, 4H), 6.41 (d/s, 2H), 6.79 (t, 1H); m/z 197.
100% With hydrogen In ethanol at 20℃; for 18 h; Description 2: 3-Fluoro-4-(4-morphoIinyl)aniline; ,o.^N4-(2-Fluoro-4-nitrophenyl)morpholine (D1; 42.6g, 0.19mol) in ethanol (1.2L) was hydrogenated over 10percentPd/C paste (4g) at NTP for 18h. The resulting mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to afford the title product (36.9g, 100percent) aes a colourless solid. 1H NMR (CDCI3) 8: 2.96 (4H, m), 3.55(2H, br s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1H, m).
100% With hydrogen In ethanol for 18 h; Description 2: 3-Fluoro-4-(4-morpholinyl)aniline; 4- (2-Fluoro-4-nitrophenyl)morpholine D1 (42.6g, 0.19mol) in ethanol (1.2L) was hydrogenated over 10percentPd/C paste (4g) at NTP for 18h. The resulting mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to afford the title product (36.9g, 100percent) as a colourless solid. 1H NMR (CDCl3) 8: 2.96 (4H, m), 3.55 (2H, s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1 H, m).
100% With hydrogen In ethanol for 18 h; 4-(2-Fluoro-4-nitrophenyl)morpholine D1 (42.6g, 0.19mol) in ethanol (1.2L) was hydrogenated over 10percentPd/C paste (4g) at NTP for 18h. The resulting mixture was filtered through Kieselguhr and the filtrate evaporated in vacuo to afford the title product (36.9g, 100percent) as a colourless solid. 1H NMR (CDCI3) δ: 2.96 (4H, m), 3.55 (2H, s), 3.84 (4H, m), 6.41 (2H, m), 6.79 (1 H, m).
99% With hydrogen In ethanol; ethyl acetate at 20℃; for 18 h; General procedure I.3-FIuoro-4-morpholin-4-yl-phenylamineTo a solution of 4-(2-fluoro-4-nitro-phenyl)-morpholine (leqv, 1.675 g, 8.54 mmol) in EtOH (40 ml) at room temperature under a nitrogen atmosphere was added palladium on carbon (10percent by Wt, 0.200 g). The reaction suspension was placed under a hydrogen atmosphere (ca. 1 atm) and stirred at room temperature for 18 hrs.The black suspension was filtered through celite, to remove the palladium on carbon, and evaporated at reduced pressure to give the desired product as a grey powder (1.656 g, 99percent, 8.44 mmol). LC/MS: 100percent MH+, m/z 197, Rt " 0.20 mins.
98.3% With hydrogen In ethyl acetate at 80℃; for 0.00833333 h; (7) Weigh 200g of the intermediate 4- (2-fluoro-4-nitrophenyl) morpholine obtained in the previous step and dissolve it in 880mL of ethyl acetate. Stir to dissolve and add 4g of 10percent Pd / C as material 6; (8) Adjusting the flow rate of the slurry pump The flow rate of the material 6 is 18.8 g / min, the flow rate of the H2 gas flow meter is adjusted to be 650 ml / min, the reaction temperature is 80 ° C.,The molar ratio of 4- (2-fluoro-4-nitrophenyl) morpholine to H2 is 1: 3.5, the residence time of the reaction is 30s and the reaction pressure is 0.5 MPa. (9) After each batch of material in the reactor reaches a steady state, the reaction solution flowing out from the outlet of the reactor is collected to flow in for 6 minutes (ie 1880 g of material 6,187.3 g of 4- (2-fluoro-4-nitrophenyl) morpholine) as an example, palladium carbon was removed by filtration and the filtrate was spin-dried to give a brown crystalline powder,After vacuum drying at 40 ° C, 159.7 g of the final product 3-fluoro-4- (4-morpholinyl) aniline was obtained in a yield of 98.3percent and a liquid phase purity of 99.5percent.
95% With hydrogen In ethanol for 3 h; 4-(2-Fluoro-4-nitrophenyl)morpholine (7.70 g, 33.62 mmol) was taken up in EtOH (100 ml.) and 10percent Palladium/Carbon (0.500 g) was added. The mixture was stirred under H2, 60 psi, for 3 h. The reaction mixture was filtered through a celite plug and the solvent was removed to give 6.40 g, 95percent yield, of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.71 - 6.80 (m, 1 H), 6.27 - 6.35 (m, 2 H), 4.97 (s, 2 H), 3.65 - 3.68 (m, 4 H), and 2.77 - 2.80 (m, 4 H).
95% With ammonium formate In ethyl acetate for 8 h; Example 2
Preparation of 3-fluoro-4-morpholinyl aniline
10percent Pd-C 4.0 g was added to 3-fluoro-4-morpholinyl nitrobenzene (40 g, 177 mmol), ammonium formate (50 g, 793 mmol) in 200 mL of ethyl acetate and stirred at 4550° C. for 8 h until the completion of the reaction.
The mixture was then filtrated and separated by water.
The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 33 g of solid in 95percent yield.
1H NMR (300 MHz, CDCl3) δ: 3.01 (m, 4H, CH2CH2N), 3.56 (br, 2H, ArNH23.86 (m, 4H, CH2CH2O), 6.41 (m, 2H, ArH), 6.79 (m, 1H, ArH)
95% With ammonium formate In ethyl acetate at 45 - 50℃; for 8 h; 10percent Pd-C 4.0 g was added to 3-fluoro-4-morpholinyl nitrobenzene (40 g, 177 mmol), ammonium formate (50 g, 793 mmol) in 200 mL of ethyl acetate and sirred at 45.similar.50°C for 8h until the completion of the reaction. The mixture was then filtrated and separated by water. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to provide 33 g of solid in 95 percent yield. 1H NMR (300MHz, CDCl3) δ: 3.01 (m, 4H, CH2CH2N), 3.56 ( br , 2H , ArNH2 3.86 (m, 4H, CH2CH2O), 6.41 (m, 2H, ArH), 6.79 (m, 1H, ArH) HPLC : 99.0percent.
92% With ammonium formate In tetrahydrofuran; methanol at 20℃; Inert atmosphere; cooling with ice EXAMPLE 5. 3-Fluoro-4-morpholinoaniline (5). Alternative procedure. 3-Fluoro-4-morpholinonitrobenzene (2) (12.6 gm, 55.67mmol) and ammonium formate (14.45 gm, 229 mmol) was added to a 3-neck 500 ml rd bottom flask with football stirrer. Methanol (135 ml) and reagent grade THF (35 ml) were added to the flask. The mixture was warmed to obtain a homogenous solution and ammonium formate (14.45 gm, 229 mmol) was added forming a homogenous solution. The reaction was cooled in an ice bath and the flask was alternately evacuated (House vac) and filled with argon (4 X) (Firestone valve). 10percent Pd/C (335 mgs) was added and the reaction was evacuated (House vac) and filled with argon (2X) and was stirred in an ice bath overnight allowing the reaction to warm to room temperature. The water-white reaction (when stirring stopped and catalyst allowed to settle) was treated with solid sodium ascorbate (3 gm) and diluted with methylene chloride (150 ml). The reaction was decanted from the dark solid (catalyst and salts) into a 1 L separatory funnel. The dark solid was washed/decanted with additional methylene chloride (75 ml) that was added to the separatory funnel. Brine (175ml, containing 2 gm sodium ascorbate) was added to the seperatory funnel and the organic layer separated. The aqueous layer was extracted with additional methylene chloride (75 ml). The combined organic layers were washed with brine (2 x 75 ml containing 1 gm sodium ascorbate) (to remove MeOH - and water), dried (MgS04), and evaporated providing a yellow orange crystalline solid (10 gm, 92percent). TLC (silica gel, CHC13) Rf = 0.18 (spot turns brown on exposure to UV light). Material used immediately in the next step (should be stored under argon or nitrogen until used).
92.6% With iron; ammonium chloride In ethanolReflux A solution of 3-fluoro-4-morpholino-nitrobenzene (5.14 g, 22.7 mmol)NH4Cl (6.22 g, 116.0 mmol) in ethanol, reductive iron powder (4.46 g, 79.5 mmol)Stirring, heating to reflux reaction, TLC monitoring, reaction is completed, filtration,The filtrate was concentrated and the residue was cooled and filtered. The filter cake was washed with water and dried to give 4.12 g of product as a brown powdery solid product, 3-fluoro-4-morpholinoaniline, in a yield of 92.6percent.
90% With hydrogen In methanol; ethanolamine at 20℃; Example-2: Preparation of 3-fluoro-4-morpholinylaniline (V) 3-Fluoro-4-morpholinylnitrobenzene (100 g) was dissolved in a mixture of methanol (900 ml) and ethanolamine (10 ml). To the resulting solution, Raney nickel (20 g) was added. Hydrogenation was carried out under 5 kg/cm2 hydrogen pressure at room temperature. After the completion of reaction, the reaction mass was filtered and washed with methanol. The filtrate was concentrated. To the resulting residue water (100 ml) was added and concentrated. The residue was cooled to room temperature and diluted with water (500 ml). The resulting suspension was stirred for lh. The solid mass was filtered, washed with water and dried to obtain the titled compound (78 g) with 90percent yield.
89.5% With palladium 10% on activated carbon; ammonium formate In acetone at 45 - 50℃; for 4 h; 36.2 g (0.16 mol) 3-fluoro-4-morpholinylnitrobenzene, 3.2 g 10percent Pd/C, 30.4 g (0.49 mol) ammonium formate and 500 ml acetone were added into a 1000 ml four-necked bottle equipped with reflux condenser and dropping funnel, and stirred for 4 hours at 45˜50° C.
After the completion of the reaction traced by TLC (developing solvent: ethyl acetate:petroleum ether=1:1), it was cooled to room temperature.
After filtering by suction, solvents were evaporated from the filtrate under reduced pressure to obtain crude solid, which was recrystallized from toluene to obtain 28.1 g solid (89.5percent yield).
Structural confirmation:
1HNMR(δ, ppm, 400 MHz , CDCl3): 2.983(s, 4H, (-CH2-N) 2); 3.606 (s, 2H, NH2); 3.863 (s, 4H, (-CH2-O)2); 6.407(d, 1H, J=8.0, Ar-H); 6.435(d, 1H, J=13.6, Ar-H); 6.828(s, 1 H, Ar-H);
13CNMR(δ, ppm, 400 MHz , CDCl3): 51.74, 51.76; 67.16; 103.76, 104.00; 110.60, 110.62; 120.22, 120.27; 131.64, 131.73; 142.83, 142.93; 155.53, 157.97
89% With hydrogen; palladium In tetrahydrofuran at 20℃; for 12 h; To a solution of 4-(2-fluoro-4-nitrophenyl) morpholine (15.0 g, 66 mmol) in THF (100 mL) was added Pd/C (3.0 g). The reaction mixture was stirred at rt under H2 for 12 h. The mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give the title compound as a white solid (11.55 g. 89percent).
89% With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; for 12 h; To a solution of 4-(2-fluoro-4-nitrophenyl)morpholine (15.0 g, 66 mmol) in THF (100 mL) was added Pd/C (3.0 g).
The reaction mixture was stirred at rt under H2 for 12 h.
The mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo to give the title compound as a white solid (11.55 g, 89percent).
89% With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; for 12 h; Palladium on carbon (3.0 g) was added to a solution of 4-(2-fluoro-4-nitrophenyl)morpholine (15.0 g, 66 mmol) in tetrahydrofuran (100 mL) and the mixture was bubbled with hydrogen and stirred for 12 h at room temperature.The mixture was filtered through celite and the filtrate was evaporated to dryness under reduced pressure to give a white solid (11.55 g, 89percent).
88% With hydrogen In ethyl acetate for 5 h; 3-2-2:
Preparation of (3-fluoro-4-morpholino)aniline
To 120 ml of ethyl acetate were sequentially added 4.2 g (18.6 mmol) of (3-fluoro-4-morpholino)nitrobenzene synthesized in Preparation Example 3-2-1 and 420 mg (10 W percent) of Pd/C, followed by reaction in a hydrogen reactor under hydrogen pressure of 4bar for 5 hours.
After the reaction was complete, Pd/C was filtered through celite.
The filtrate was distilled under reduced pressure, purified by recrystallization from ethyl acetate and n-hexane and then dried under vacuum at about 40° to afford 3.2 g (yield: 88percent) of the desired compound.
Mass (M+): 197.1
1H-NMR (DMSO-d6): 2.80(brm, 4H), 3.68(brm, 4H), 4.99(brs, 2H), 6.33(m, 2H), 6.76(t, 1H).
88% With hydrogen In ethyl acetate for 5 h; Example 3-2-2 Preparation of (3-fluoro-4-morpholino)aniline To 120ml of ethyl acetate were sequentially added 4.2g (18.6 mmol) of (3-fluoro-4-morpholino)nitrobenzene synthesized in Preparation Example 3-2-1 and 420mg (10Wpercent) of Pd/C, followed by reaction in a hydrogen reactor under hydrogen pressure of 4bar for 5 hours. After the reaction was complete, Pd/C was filtered through celite. The filtrate was distilled under reduced pressure, purified by recrystallization from ethyl acetate and n-hexane and then dried under vacuum at about 40°C to afford 3.2g (yield: 88percent) of the desired compound. Mass (M+): 197.1 1H-NMR (DMSO-d6): 2.80(brm, 4H), 3.68(brm, 4H), 4.99(brs, 2H), 6.33(m, 2H), 6.76(t, 1H).
82.59% With ammonium formate In tetrahydrofuran; methanol for 3 h; To a suspension of 365.6 g of 3-fluoro-4-morpholinyl-nitrobenzene and 488.4 g of ammonium formate in 1 L of tetrahydrofuran and 4.40 L of methanol under nitrogen was added 5.24 g of 10percent palladium/carbon. After stirring the mixture for 3 hrs, the mixture was filtered. The obtained filtrate was concentrated and 2 L of water was added to the obtained reaction mass and was extracted with 3.50 L of ethyl acetate. The organic layer was concentrated to give a brown solid. Yield: 295 g.; Percentage: 82.59percent w/w
105 g With hydrogen In methanol at 45 - 50℃; for 8 h; Autoclave; Inert atmosphere Methanol (1.35 Lt) and 3-fluoro-4-morpholinyl nitrobenzene (134 gr) are added into autoclave and followed by Raney Nickel (20.5 gr). The system was flushed with nitrogen and hydrogen gas. The pressure of hydrogen was set to 4.0 kg/cm−2. The reaction mixture was stirred at 45-50° C. under H2 pressure for 8 hrs & the reaction followed by TLC until completion. The reaction mixture was filtered through celite and the filtrate is distilled off evaporate solvent completely U/vaccum at temperature. Reaction mass is cooled to 25-30° C. To this DM water (400 ml) is added, Stirred for 1 hr at 25-30° C. The solid is filtered to give 105 gr of 3-fluoro-4-morpholinyl aniline
92 mg With 5%-palladium/activated carbon; hydrogen In methanol at 22 - 35℃; In a catalytic pressure hydrogenation vessel were added methanol (800 ml), and Compound-I (115 gms) as obtained above. The reaction mass was stirred to dissolve Compound-I while maintaining temperature at 22°-28°C. Palladium — Carbon Catalyst (5percent, 2.15 gm) was then introduced. The reaction mass was flushed with nitrogen gas and then with hydrogen gas. Catalytic hydrogenation process was carried out with hydrogen pressure (0.3 kg/cm2 — 2.0 kg/cm2) and temperature (28°-35°C) for a period of 2-4 hrs, while monitoring reaction progress by TLC. After completion of reaction, the mass was cooled to 20°-25°C, filtered to remove the catalyst and concentrated to remove methanol partially (580 ml — 630 ml) at 45°-52°C. Reaction mass turned into thick slurry. It was added with water (390 ml), stirred for half an hour, cooled to 20°-25°C, filtered, washed with cold water (120-150 ml), and finally dried at 60°-65°C in a tray drier to obtain compound-lI (92 gms).
96 g With palladium 10% on activated carbon; ammonium formate In acetone at 50℃; for 8 h; 3L in three-mouth bottle, with mechanical stirring and the thermometer, respectively, by adding 3-fluoro-4-morpholine nitrobenzene 100g (0.44mol), acetone 1L, 10percent Pd/C3 . 0g and ammonium formate 137.5g (2.18mol), fully stirring, the temperature is increased to 50 °C, stirring reaction 8h, TLC showed reaction has been completed, and then adding acetone 500 ml, stir, aging 2h, filtering, the filtrate concentrated to dry, getting white solid 96g, without purification of the product, directly used for the next step reaction.

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4-(4-Fluoro-2-nitrophenyl)morpholine

Similarity: 0.87

Chemical Structure| 218301-62-3

[ 218301-62-3 ]

4-(3-Fluoro-4-nitrophenyl)morpholine

Similarity: 0.96

Chemical Structure| 1233955-40-2

[ 1233955-40-2 ]

4-(2-Fluoro-6-nitrophenyl)morpholine

Similarity: 0.92

Related Parent Nucleus of
[ 2689-39-6 ]

Morpholines

Chemical Structure| 218301-62-3

[ 218301-62-3 ]

4-(3-Fluoro-4-nitrophenyl)morpholine

Similarity: 0.96

Chemical Structure| 1233955-40-2

[ 1233955-40-2 ]

4-(2-Fluoro-6-nitrophenyl)morpholine

Similarity: 0.92

Chemical Structure| 218301-62-3

[ 218301-62-3 ]

4-(3-Fluoro-4-nitrophenyl)morpholine

Similarity: 0.96

Chemical Structure| 1233955-40-2

[ 1233955-40-2 ]

4-(2-Fluoro-6-nitrophenyl)morpholine

Similarity: 0.92

Chemical Structure| 238418-75-2

[ 238418-75-2 ]

4-(4-Fluoro-2-nitrophenyl)morpholine

Similarity: 0.87