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Chemical Structure| 223404-63-5

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Product Details of [ 223404-63-5 ]

CAS No. :223404-63-5
Formula : C11H14N2O3
M.W : 222.24
SMILES Code : O=[N+](C1=CC=C(N2CCOCC2)C(C)=C1)[O-]
MDL No. :MFCD11039650
InChI Key :LQPUAYMERQENBC-UHFFFAOYSA-N
Pubchem ID :10799042

Safety of [ 223404-63-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 223404-63-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 223404-63-5 ]

[ 223404-63-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 223404-63-5 ]
  • [ 112900-82-0 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen In ethanol; toluene Step 2: A suspension of 4-(2-methyl-4-nitro-phenyl)-morpholine (0.53g, 2.4mMol) and 10percent palladium on carbon (55mg) in 1:1 toluene : ethanol (25ml) was placed under an atmosphere of hydrogen, using standard procedures, until reaction was complete. The reaction mixture was filtered through a pad of celite, which was then washed with ethanol. The filtrates were reduced under vacuum to give 3-methyl-4- morpholin-4-yl-phenylamine as a tan solid.( 0.47g , 100percent), LC/MS: RT - 2.66, MH+ 193; No. (CDCl3) 6.82 (1H, d, J 8.2Hz) ; 6.48-6.54 (2H, m) ; 3.76 (4H, t, J 4.4Hz) ; 2.76 (4H, t, J 4.4Hz); 2.18 (3H, s)
96.35% With ammonium chloride; zinc In methanol at 0 - 20℃; for 1 h; To a stirred mixture of 4-(2-methyl-4-nitrophenyl)morpholine (6 g, 0.0645 mol, 1.0 eq), Zn dust (8.64 g, 0.135 mol, 5 eq) in methanol (50 mL) in a round bottomed flask at 0°C, ammonium chloride (7.29 g, 0.135 mol, 5 eq) was added slowly and the mixture stirred at rt for 1 h while monitoring by TLC. After completion of the starting material, the reaction mass was filtered through a Celite® bed and filtrate was concentrated under reduced pressure to obtain a residue. The residue was diluted with DCM (150 mL) and washed with water. The organic layer was separated, washed with brine sol, dried over sodium sulphate and concentrated under reduced pressure to obtain 3-methyl-4- morpholinoaniline as brown solid (5 g, 96.35percent). 1H NMR (400 MHz, CDC13): δ 6.768 (d, 1H), 6.39 (s, 1H), 6.36 (d, 1H), 4.66 (brs, 2H), 3.681 (t, 4H), 2.683 (t, 4H), 2.124 (s, 3H).
86% With hydrogenchloride; iron In ethanol; water at 90℃; for 12 h; Inert atmosphere 4-(2-Methyl-4-nitrophenyl)morpholine (2.60 g, 11.70 mmol), iron powder (3.28 g, 58.50 mmol), BAlcohol (40mL), water (5mL) and hydrochloric acid (0.1g, 35percent aqueous solution) were added to a 100mL single-mouth bottle, heated under nitrogen and heated toStir at 90 ° C for 12 hours. After completion of the reaction, the mixture was filtered, and the filtrate was evaporated.The mixture was washed with water (30 mL×3)The title compound (yellow solid, 1.93 g, yield: 86percent).
References: [1] Patent: WO2005/105761, 2005, A1, . Location in patent: Page/Page column 36.
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 5099 - 5119.
[3] Patent: WO2015/38417, 2015, A1, . Location in patent: Page/Page column 94; 95.
[4] Patent: CN108690043, 2018, A, . Location in patent: Paragraph 0262; 0266-0267.
[5] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 4, p. 353 - 360.
 

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