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Chemical Structure| 125422-83-5 Chemical Structure| 125422-83-5

Structure of 125422-83-5

Chemical Structure| 125422-83-5

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Product Details of [ 125422-83-5 ]

CAS No. :125422-83-5
Formula : C7H14BrNO
M.W : 208.10
SMILES Code : BrCCCN1CCOCC1
English Name :4-(3-Bromopropyl)morpholine
MDL No. :MFCD09998837

Safety of [ 125422-83-5 ]

Application In Synthesis of [ 125422-83-5 ]

* 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 [ 125422-83-5 ]

[ 125422-83-5 ] Synthesis Path-Downstream   1~4

  • 1
  • C9H6N2O3(2-)*2Na(1+) [ No CAS ]
  • [ 125422-83-5 ]
  • [ 199327-61-2 ]
YieldReaction ConditionsOperation in experiment
93.8% With 1-butyl-3-methylimidazolium Tetrafluoroborate; In tetrahydrofuran; at 65 - 70℃; for 5h; The compound of Formula III disodium salt (7.1g, 30mmol) in 20mL THF was followed by the addition fo 5percent [Bmim]BF4 and the addition of Formula IV (X=Br) (7.5g, 36mmol) and was heated to about 65-70°C for 5.0 hours. The reaction mixture was suction filtered to remove the resulting white solid NaBr. The solvent was distilled THF and was added with 20mL distilled water. 0.5M hydrochloric acid was added to adjust to pH to 6-7 and stirred at room temperature. The water vapor was distilled off and Formula 1 was obtained (9.0g, 93.8percent yield).
  • 2
  • [ 574745-97-4 ]
  • [ 367-21-5 ]
  • [ 125422-83-5 ]
  • [ 184475-35-2 ]
YieldReaction ConditionsOperation in experiment
5.8 g With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h; Example 1: One kind of gefitinib preparation method, the steps of: three-necked flask 2.0gDMF, 30mL thionyl chloride and 2.9g of raw materials 1 (quinazolin-4-one, 20mmol), was heated to 80 reaction was stirred 3h.After the reaction, the solvent was distilled off under reduced pressure and the unreacted chlorinating agent, to the residue was added 20mL of toluene, concentrated under reduced pressure, was repeated three times.The resulting solid was dissolved in 250mLDMF, followed by adding 8.3gK2CO3, 6.2g side chain 3 (bromopropyl morpholino) side chains and 4.4g 4 (fluorochloroaniline), heated to 90 reaction was stirred 3h.After completion of the reaction, cooled to room temperature, stirring slowly added 1000mL of water, stirring was continued for 2h, after filtration and drying was 6g gefitinib crude.The crude product is recrystallized from ethyl acetate to give 5.8g white powder gefitinib
  • 3
  • [ 2137975-63-2 ]
  • [ 125422-83-5 ]
  • [ 2138302-00-6 ]
YieldReaction ConditionsOperation in experiment
72.9% With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;
52.9% With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; Inert atmosphere; 23.1 (1) Preparation of 4-chloro-3-(3-morpholinopropoxy)-5-nitrobenzamide Dissolve 4-chloro-3-hydroxy-5-nitrobenzamide (0.2g, 0.93mmol), 3-bromopropylmorpholine (182mg, 1.12mmol) and potassium carbonate (0.167g, 1.2mmol) in 100ml N,N-dimethylformamide was reacted at 70°C for 4h under argon protection. After the reaction, 30 ml of saturated ammonium chloride solution was added, the mixture was extracted three times with dichloromethane, washed twice with distilled water, washed once with saturated sodium chloride solution, and dried with sodium sulfate. Concentrate and separate by column chromatography. The eluent is dichloromethane:methanol=20:1 to obtain 0.169 g of light yellow solid, yield 52.9%, melting point 165-166°C
28.67% With caesium carbonate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere; 123 Synthesis of 123.1 To a stirred solution of 4-chloro-3-hydroxy-5-nitrobenzamide (2.00 g, 9.234 mmol, 1.00 equiv) in DMSO (25.00 mL) in a 50 mL 3-necked round-bottom flask, 4-(3- bromopropyl)morpholine (2.88 g, 13.852 mmol, 1.5 equiv) and Cs2CO3(9.03 g, 27.703 mmol, 3 equiv) were added at room temperature. The resulting mixture was stirred for 2h at 80°C under nitrogen atmosphere. The resulting mixture was extracted with EtOAc (3x25 mL). The combined organic layers were washed with brine (3x25 mL), dried over anhydrous NaiSCL. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by reverse flash chromatography with the following conditions: column, C18 silica gel; mobile phase, MeOH in water, 10% to 50% gradient in 10 min; detector, UV 254 nm. This resulted in 4-chloro-3-[3- (morpholin-4-yl)propoxy]-5-nitrobenzamide (1 g, 28.67%) (ES, m/z): [M+H] 344.1 as an off- white solid.
  • 4
  • [ 1449430-45-8 ]
  • [ 125422-83-5 ]
  • [ 267243-64-1 ]
YieldReaction ConditionsOperation in experiment
91.8% With potassium carbonate In acetonitrile at 50 - 55℃; 3 Example three: At room temperature, 4-(3-bromopropyl)-morpholine (6.24 g, 30 mmol) and solvent acetonitrile 100 mL were added to the reaction flask, and potassium carbonate (4.14 g, 30 mmol) was added with stirring until all were dissolved. Warm to 50-55°C and add 7-hydroxy-N-(3-chloro-4-fluorophenyl)-6-nitroquinazolin-4-amine (V) (3.34g, 10mmol) with stirring, continue The reaction was stirred for 6-8 hours, and the reaction was completed by TLC. Cool to room temperature, add water and adjust the pH to neutral with dilute hydrochloric acid, solid precipitates, crystallize slowly at 05 for 2-3 hours, filter with suction and dry under reduced pressure to obtain N-(3-chloro-4-fluorophenyl )-7-(3-morpholin-4-propoxy)-6-nitroquinazolin-4-amine (III) 4.23g, yield 91.8%.
 

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