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Structure of 91271-65-7

Chemical Structure| 91271-65-7

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Product Details of [ 91271-65-7 ]

CAS No. :91271-65-7
Formula : C12H17NO2
M.W : 207.27
SMILES Code : OCC1=CC=C(CN2CCOCC2)C=C1
MDL No. :MFCD04974050
InChI Key :MWVQMAWLNHACQK-UHFFFAOYSA-N
Pubchem ID :2795499

Safety of [ 91271-65-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 91271-65-7 ]

* 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 [ 91271-65-7 ]

[ 91271-65-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 91271-65-7 ]
  • [ 82413-63-6 ]
YieldReaction ConditionsOperation in experiment
93% With manganese(IV) oxide; In dichloromethane; at 20℃; for 72h; Step 3) 4-Morpholin-4-ylmethyl-benzaldehyde Manganese dioxide (3.28 g, 37.67 mmol) was added to a stirred solution of (4-morpholin-4- ylmethyl-phenyl)-methanol (1.3g, 6.28 mmol) in methylene dichloride (120 mL) at rt and stirred for 72 h. The reaction mixture was filtered through sintered funnel using celite and washed with methylene dichloride (50 mL). The solvent was evaporated under reduced pressure and purifiedby column chromatography (silica gel, 20% EtOAc/Hexanes) to give 4-morpholin-4-ylmethyl- benzaldehyde (1.2 g, 93%) as a white solid. MS calcd. for C12H15N02 [(M+H)?i 206, obsd.
88% Protection of the nitrogen at -70 C (COCl)2 (152mg, 1.2mmol) was added to DMSO (156mg, 2.0mmol) in DCM (10 mL), and stirring was continued to maintain a temperature of -70 C for 30 minutes, followed by addition of 4-(morpholinylmethyl)benzyl alcohol (207mg, 1.0mmol) 3mL DCM the solution stirred for 1 hour. Instillation of Et3N (405mg, 4.0mmol), maintaining the temperature at -70 C and stirring was continued for 1 hour was raised to 25 C, dropwise addition of water (10 mL) to quench the reaction, was added NaHCO3 solution (5mL). Liquid separation, the aqueous phase was extracted with 10mLDCM combined organic phase was concentrated after column chromatography (PE:EtOAc = 2:1) as a pale yellow oily product A405A (180mg, yield: 88%).
81% To a solution of 4-bromoethyl-benzoic acid ethyl ester (4.0 g, 16.46 mmol) in THF (30 mL), morpholine (2.87 g, 32.92 mmol) was added and the reaction mixture was stirred for 48 h at room temperature. The reaction mixture was diluted with water and the product was extracted with ethyl acetate. The combined organic layers were washed with water, brine, and dried over Na2SO4. The solvent was removed to give 3.4 g of crude product in 83% yield.LAH (0.571 g, 15.05 mmol) was added to a 3-neck dry flask and THF (50 mL) was added on cooling. A solution of 4-morpholin-4-ylmethyl)-benzoic acid ethyl ester (3.0 g, 12.04 mmol) in THF (10 mL) was added slowly on cooling. After completion of addition, the reaction mixture was heated at reflux for 3 h. The reaction mixture was cooled to 0 C. and a 10% NaOH solution was added carefully followed by water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine and dried over Na2SO4. The solvent was removed to give (4-morpholin-4-ylmethyl phenyl)methanol (2.0 g, 80%). To the 3-flask anhydrous CH2Cl2 (100 mL) was added and cooled to -78 C. Oxalyl chloride (1.47 g, 11.59 mmol) and DMSO (1.5 g, 19.32 mmol) were added at -78 C. The reaction mixture was stirred for 15 min at -78 C. A solution of (4-morpholin-4-ylmethyl phenyl)methanol (2.0 g, 9.66 mmol) in CH2Cl2 (10 mL) was added at -78 C. and the mixture was stirred at -78 C. for 1 h. Then, Et3N (3.9 g, 38.64 mmol) was added. The reaction mixture was allowed to come at room temperature. Water was added and the organic layer was isolated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, brine and dried over Na2SO4. Then solvent was removed to give crude 4-morpholin-4-ylmethyl benzaldehyde (1.6 g, 81%).To a solution of 2-amino-4,6-dimethoxy-benzamide (150 mg, 0.76 mmol) and 4-morpholin-4-ylmethyl benzaldehyde (156 mg, 0.76 mmol) in N,N-dimethyl acetamide (10 mL), NaHSO3 (150 mg, 0.84 mmol) and p-TSA (174 mg, 0.91 mmol) were added and the reaction mixture was heated at 150 C. for 5 h. The reaction mixture was cooled to room temperature, water was added and the mixture was neutralized with NaHCO3. The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography to give 5,7-dimethoxy-2-(4-(morpholinomethyl)phenyl)quinazolin-4(3H)-one, which was converted to the hydrochloride salt (165 mg, 51%). Selected data: MS (ES) m/z: 382.07; MP 206-208 C. (at decomposition).
With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78℃; for 1h; To the 3-flask anhydrous CH2Cl2 (100 mL) was added and cooled to -78 C. Oxalyl chloride (1.47 g, 11.59 mmol) and DMSO (1.5 g, 19.32 mmol) were added at -78 C. The reaction mixture was stirred for 15 min at -78 C. A solution of (4-morpholin-4-ylmethyl phenyl)methanol (2.0 g, 9.66 mmol) in CH2Cl2 (10 mL) was added at -78 C. and the mixture was stirred at -78 C. for 1 h. Then, Et3N (3.9 g, 38.64 mmol) was added. The reaction mixture was allowed to come at room temperature. Water was added and the organic layer was isolated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, brine and dried over Na2SO4. Then solvent was removed to give crude 4-morpholin-4-ylmethyl benzaldehyde (1.6 g, 81%).

 

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