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Chemical Structure| 77279-24-4 Chemical Structure| 77279-24-4

Structure of 77279-24-4

Chemical Structure| 77279-24-4

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Product Details of [ 77279-24-4 ]

CAS No. :77279-24-4
Formula : C11H22N2O3
M.W : 230.30
SMILES Code : CC(C)(C)OC(=O)N1CCN(CCO)CC1
MDL No. :MFCD00728947
InChI Key :VRXIOAYUQIITBU-UHFFFAOYSA-N
Pubchem ID :735736

Safety of [ 77279-24-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H410
Precautionary Statements:P273-P301+P310-P305+P351+P338
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 77279-24-4 ]

* 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 [ 77279-24-4 ]

[ 77279-24-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 54589-54-7 ]
  • [ 77279-24-4 ]
  • [ 191483-37-1 ]
  • 2
  • [ 77279-24-4 ]
  • [ 655225-01-7 ]
YieldReaction ConditionsOperation in experiment
83.7% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20℃;Cooling with ice; Carbon tetrabromide (1.681 g, 5.07 mmol) was dissolved in dichloromethane (17 ml), cooled with ice.thereTertiary butyl 4- (2-hydroxyMethyl) piperazine-1-carboxylate (1.062 g, 4.61 mmol), triphenylphosphine (1.329 g, 5.07 mmol), and stirred overnight at room temperature was added dichloromethane (11 ml). After the reaction, the solvent was evaporated. The residue was purified by silica gel column chromatography (SNAP ULTRA 25 g, hexane / ethyl acetate) to give the title compound (1.131 g, 83.7percent) as a yellow solid.
78% With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20℃; for 20h; STEP A: A solution of tetrabromomethane (1.58 g, 4.7 mmol) in DCM (10 mL) is added dropwise (30 min) to the solution of N-Boc-piperazin-4-ethanol (1 g, 4.34 mmol) and triphenylphosphine (1.23 g, 4.7 mmol) in DCM (10 mL) at 0°C. The reaction is left at RT for 20 h. The organic solvent is removed under reduced pressure and the crude is purified by flash column chromatography (eluent petroleum ether/EtOAc) to give the expected compound (1 g, 3.38 mmol, Yield 78percent) as colourless oil. H1-NMR (CDCI3) delta (ppm): 3.41-3.47 (m, 6H); 2.81 (t, J=6.00 Hz, 2H); 2.48 (t, J=6.00 Hz, 4H); 1.46 (s, 9H)
With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; Example 63; l-{2-[4-(3,5-dimethoxybenzyl)piperazin-l-yl]ethyl}-3,3-bis(4-fluorophenyl)pyrrolidin-2- one; Example 63A; tert-butyl 4-(2-bromoethyl)piperazine-l-carboxylate; tert-Butyl 4-(2-hydroxyethyl)piperazine-l-carboxylate (5.76 g, 25.0 mmol) was dissolved in dry tetrahydrofuran (100 mL) and carbon tetrabromide (9.12 g, 27.5 mmol). A solution of triphenyl phosphine (6.62 g, 25.3 mmol) in dry tetrahydrofuran (25 mL) was added dropwise, and the mixture was stirred for 20 hours. The reaction was diluted with n- hexane (100 mL) and washed with a saturated NaHCO3 solution, water and brine, dried with MgSO4, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexanes 1 :4 gave the title compound. MS (DCI) m/z 295(M+H)+.
  • 3
  • [ 68631-52-7 ]
  • [ 77279-24-4 ]
  • [ 1268810-28-1 ]
YieldReaction ConditionsOperation in experiment
4.10. Diethyl 4-[2-(4-(tert-butoxycarbonyl)piperazin-1-yl)ethoxy]pyridine-2,6-dicarboxylate 4.5 ml of TEA and then 2 ml of methanesulphonyl chloride are added to a solution, cooled to 0 C., of 5 g of 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperazine in 102 ml of DCM. After 1 h, the mixture is brought back to AT. After stirring for an additional 1 h, the mixture is hydrolysed and the organic phase is washed 2* with water, then dried over MgSO4 and concentrated under RP. 140 ml of DMF are added to the residue thus obtained (6.7 g) and the mixture is brought to 60 C. 190 mg of the diethyl ester of chelidamic acid (Scrimin P., Tecilla P., Tonellato U. and Vendrame T. J., Org. Chem., 1989, 54, 5988) and 549 mg of K2CO3 are then added and the mixture is heated at 80 C. for 20 h. After concentrating under RP, the mixture is hydrolysed and extracted 3* with AcOEt, the combined organic phases are washed with a saturated NaCl solution and concentrated under RP, and the residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-150 g) using a gradient from 60 to 85% of AcOEt in heptane. 3.1 g of diethyl 4-[2-(4-(tert-butoxycarbonyl)piperazin-1-yl)ethoxy]pyridine-2,6-dicarboxylate are thus obtained. 1H NMR (400 MHz, d6-DMSO): 1.34 (t, J=7.2 Hz, 6H); 1.39 (s, 9H); 2.44 (m, 4H); 2.76 (t, J=5.7 Hz, 2H); 3.30 (partially masked m, 4H); 4.34 (t, J=5.7 Hz, 2H); 4.38 (q, J=7.1 Hz, 4H); 7.74 (s, 2H). LC/MS (B): rt=2.81 min; [M+H]+: m/z 452; [MH+HCO2H]-: m/z 496.
 

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Technical Information

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