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Chemical Structure| 30668-14-5 Chemical Structure| 30668-14-5

Structure of 30668-14-5

Chemical Structure| 30668-14-5

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Product Details of [ 30668-14-5 ]

CAS No. :30668-14-5
Formula : C7H13NO2
M.W : 143.18
SMILES Code : CCC(N1CCOCC1)=O
English Name :1-Morpholinopropan-1-one
MDL No. :MFCD03208781

Safety of [ 30668-14-5 ]

Application In Synthesis of [ 30668-14-5 ]

* 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.

  • Downstream synthetic route of [ 30668-14-5 ]

[ 30668-14-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 30668-14-5 ]
  • [ 159603-71-1 ]
  • [ 1160827-82-6 ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: t-butyl N-(6-chloro-2-pyridinyl)carbamate With n-butyllithium In tetrahydrofuran; hexane at -50 - 0℃; Stage #2: 1-morpholinopropane-1-one In tetrahydrofuran; hexane at -40℃; for 1h; 34A tert-Butyl (6-chloro-3-propanoylpyridin-2-yl)carbamate Example 34A tert-Butyl (6-chloro-3-propanoylpyridin-2-yl)carbamate Under argon, 7.00 g (30.6 mmol) of tert-butyl (6-chloropyridin-2-yl)carbamate (Example 11A) were initially charged in 90 ml of THF and cooled to -50° C. 47.8 ml (76.5 mmol) of butyllithium (1.6 M in hexane) were added dropwise. After the dropwise addition had ended, the reaction was slowly warmed to 0° C. and kept at 0° C. for 1 h. The mixture was then again cooled to -40° C., and 9.85 g (61.2 mmol) of N-propionylmorpholine, dissolved in 10 ml of THF, were added. The reaction solution was stirred at -40° C. for 1 h and then, at -40° C., put into 1 l of ethyl acetate and 350 ml of ammonium chloride solution, and the organic phase was separated off and washed with water and saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulphate and concentrated on a rotary evaporator. The crude product was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1). This gave 2800 mg (32% of theory) of the product. LCMS (method 6): Rt=2.13 min. (m/z=283 (M-H)-) 1H-NMR (400 MHz, DMSO-d6): δ=10.53 (br s, 1H), 8.19 (d, 1H), 7.31 (d, 1H), 2.94 (q, 2H), 1.45 (s, 9H), 1.06 (t, 3H).
32% Stage #1: t-butyl N-(6-chloro-2-pyridinyl)carbamate With n-butyllithium In tetrahydrofuran; hexane at -50 - 0℃; Inert atmosphere; Stage #2: 1-morpholinopropane-1-one In tetrahydrofuran; hexane at -40℃; for 1h; 23A Example 23Atert-Butyl(6-chloro-3-propanoylpyridin-2-yl)carbamate; Under argon, 7.00 g (30.6 mmol) of tert-butyl(6-chloropyridin-2-yl)carbamate (Example 3A) were initially charged in 90 ml of THF and cooled to -50° C. 47.8 ml (76.5 mmol) of butyllithium (1.6 M in hexane) were added dropwise. After the dropwise addition had ended, the reaction was slowly warmed to 0° C. and kept at 0° C. for 1 h. The mixture was then cooled again to -40° C., and 9.85 g (61.2 mmol) of N-propionylmorpholine dissolved in 10 ml of THF were added. The reaction solution was stirred at -40° C. for another 1 h and then, at -40° C., poured into 1 l of ethyl acetate and 350 ml of ammonium chloride solution, and the organic phase was separated off and washed with water and saturated aqueous sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator. The crude product was chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1). This gave 2800 mg (32% of theory) of the product.LCMS (Method 6): Rt=2.13 min. (m/z=283 (M-H)-)1H-NMR (400 MHz, DMSO-d6): δ=10.53 (br s, 1H), 8.19 (d, 1H), 7.31 (d, 1H), 2.94 (q, 2H), 1.45 (s, 9H), 1.06 (t, 3H).
  • 2
  • [ 30668-14-5 ]
  • [ 23949-50-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogen In 1,2-dimethoxyethane at 160℃; for 20h; Inert atmosphere; Autoclave; Molecular sieve;
With 1,1,3,3-Tetramethyldisiloxane; C18H21BiN(1+)*F6Sb(1-) In acetonitrile at 70℃; Schlenk technique; Inert atmosphere; Sealed tube;
With silver hexafluoroantimonate; 1,1,3,3-Tetramethyldisiloxane; 12-chloro-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine In acetonitrile at 70℃; Schlenk technique; Inert atmosphere; Sealed tube;
  • 3
  • [ 110-91-8 ]
  • [ 106-36-5 ]
  • [ 30668-14-5 ]
YieldReaction ConditionsOperation in experiment
57% With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)-amino]ruthenium(II); potassium <i>tert</i>-butylate In toluene at 120℃; for 48h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry; 2.2. General procedure for synthesis of amides General procedure: A mixture of amine (6.0 mmol), ester (3.0 mmol) and Ru-MACHO (1% mol) in toluene (3.0 mL) was placed in a flask and replaced withnitrogen gas. Then, t-BuOK (20% mol) was added in the mixture in the nitrogen gas flowing. The mixture was heated by reflux under the nitrogen atmosphere. During this time, the nitrogen gas was passed through the Schlenk line allowing the hydrogen gas to evolve from the reaction to escape the reactor. After the 48 h, the solvent was evaporated and the crude product was purified by flash chromatography on silica-gel to give the desired amides in 55-98% yields. The structures of the obtained amide swere determined by FT-IR and 1HNMR.
  • 4
  • [ 30668-14-5 ]
  • [ 50-00-0 ]
  • [ 5117-13-5 ]
YieldReaction ConditionsOperation in experiment
85.9% With sodium hydroxide at 85 - 90℃; 6 Preparation of methacryloylmorpholine To a 100 mL four-necked flask was added 5.43 g (0.040 mol) of propionylmorpholine, 12.97 g (0.16 mol) of formaldehyde solution,Catalyst NaOH 1.6g (0.040mol), keep the temperature at 85 ~ 90 , the reaction of 15 to 20 hours, the crude methacryloyl morpholine. After completion of the reaction, 30 ml of cyclohexane was added to azeotropically dehydrated, the NaOH was removed by filtration, and finally 0.012 g of p-hydroxyanisole (0.0001 mol) was added and distilled under reduced pressure to give 5.36 g of methacryloylmorpholine in a yield of 85.9 %, Purity 98.4%.
 

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