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[ CAS No. 836-59-9 ]

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2D
Chemical Structure| 836-59-9
Chemical Structure| 836-59-9
Structure of 836-59-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 836-59-9 ]

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Product Details of [ 836-59-9 ]

CAS No. :836-59-9MDL No. :MFCD01308572
Formula : C12H16BrNO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :286.17Pubchem ID :-
Synonyms :

Computed Properties of [ 836-59-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 836-59-9 ]

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Application In Synthesis of [ 836-59-9 ]

  • Downstream synthetic route of [ 836-59-9 ]

[ 836-59-9 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 3240-94-6 ]
  • [ 106-41-2 ]
  • [ 836-59-9 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; In N,N-dimethyl-formamide; at 60 - 65℃; for 17.5h;Industry scale;Product distribution / selectivity; Preparation of 4-(2-(4-Bromophenoxy)ethyl)morpholine (2)[000360] A 50 L jacketed reactor equipped with a reflux condenser and temperature probe was charged with 4-(3-chloropropyl)morpholine (2.44 kg, 0.54 mol), 4-bromophenol (2.27 kg, 0.54 mol, 1.0 equiv.), powdered potassium carbonate (6.331 kg, 1.88 mol, 3.50 equiv.), and DMF (12.2 L) and stirred. The reaction mixture was then heated to 60-65 0C and stirred overnight. After 17.5 h, the reaction mixture was cooled to 20-25 0C. The reaction mixture was charged to a different reactor equipped with bottom valve for the work-up. While maintaining a temperature between 20-300C, DI water (48.7 L) was charged to the reactor. The phases were separated. The aqueous layer was extracted with MTBE (3 x 24.4 L). To the combined organics, DI water (18.3 L) and then 6M sodium hydroxide (18.2 L) <n="82"/>were added. The mixture was stirred for 2-5 minutes and the phases were separated. The organic phase was washed with water (24.4 L) and brine (24.4 L), dried over magnesium sulfate, filtered, and concentrated to give 337Og of a yellow oil (89% crude yield, 99.4% AUC by HPLC).; Step 1: Preparation of 4-(2-(4-bromophenoxy)ethyl)morpholine (2)[000343] Several modifications to the procedure described in Example 2 for the ether synthesis were developed. When conducting the ether synthesis in the acetonitnle solvent, the reaction mixture was a very thick slurry and difficult to stir. Therefore, the solvent was changed to dimethylformamide (DMF), which generated a more manageable thin white slurry. It was also determined that rigorously dry conditions were not essential. For example, 0.3 volumes of deionized (DI) water with no detrimental effects to the purity or yield of the reaction. Due to the changes in reaction solvent to DMF, the work up was also modified. The modified work up now involved dilution with DI water and extraction with <n="76"/>MTBE. It was also convenient to conduct a basic wash with aqueous sodium hydroxide to remove any remaining 4-bromophenol.
With potassium carbonate; In water; N,N-dimethyl-formamide;Product distribution / selectivity; Step 1: Preparation of 4-(2-(4-bromophenoxy)ethyl)morpholine (2)[000343] Several modifications to the procedure described in Example 2 for the ether synthesis were developed. When conducting the ether synthesis in the acetonitnle solvent, the reaction mixture was a very thick slurry and difficult to stir. Therefore, the solvent was changed to dimethylformamide (DMF), which generated a more manageable thin white slurry. It was also determined that rigorously dry conditions were not essential. For example, 0.3 volumes of deionized (DI) water with no detrimental effects to the purity or yield of the reaction. Due to the changes in reaction solvent to DMF, the work up was also modified. The modified work up now involved dilution with DI water and extraction with <n="76"/>MTBE. It was also convenient to conduct a basic wash with aqueous sodium hydroxide to remove any remaining 4-bromophenol.
With potassium carbonate; In N,N-dimethyl-formamide; 4-(2-(4-(6-fluoropyridin-3-yl)phenoxy)ethyl)morpholine (5) was synthesized in 3 steps. Intermediate 2 was synthesizedusing an ether coupling reaction e.g., using Williamson ether synthesis. Ether formation between 4-(2-chloroethyl)morpholine (1) and 4-bromophenol was carried out in the presence of potassium carbonate and DMF to afford 4-(2-(4-bromophenoxy)ethyl)morpholine (2). Rigorously dry conditions were not essential for this reaction and a basic washwith sodium hydroxide was used to remove any remaining 4-bromophenol. In another aspect of the invention, intermediate2 is synthesized using any ether formation reaction. Intermediate 2 is synthesized starting from compound 1 containingany leaving group. For example, the skilled chemist would start with compounds of the general formula:
  • 2
  • 3-(4-chlorobenzylidene)-7-methoxychroman-4-one [ No CAS ]
  • [ 836-59-9 ]
  • 3-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-7-methoxy-4-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-chroman-4-ol [ No CAS ]
  • 3
  • 3-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-7-methoxy-chroman-4-one [ No CAS ]
  • [ 836-59-9 ]
  • 3-[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-7-methoxy-4-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-chroman-4-ol [ No CAS ]
  • 4
  • [ 194935-45-0 ]
  • [ 836-59-9 ]
  • [ 194935-47-2 ]
  • 5
  • [ 194935-44-9 ]
  • [ 836-59-9 ]
  • 1-[4-(2-morpholinoethoxy)phenyl]-2-phenyl-1-(2-thienyl)butan-1-ol [ No CAS ]
  • 6
  • [ 836-59-9 ]
  • [ 1038395-64-0 ]
  • 7
  • [ 836-59-9 ]
  • [ 1038395-63-9 ]
  • 8
  • [ 836-59-9 ]
  • [ 897016-82-9 ]
  • 9
  • [ 836-59-9 ]
  • [ 1080645-95-9 ]
  • 10
  • [ 836-59-9 ]
  • 2-(5-(4-(2-morpholinoethoxy)phenyl)pyridin-2-yl)-N-benzylacetamide dihydrochloride [ No CAS ]
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