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[ CAS No. 51639-48-6 ] {[proInfo.proName]}

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Chemical Structure| 51639-48-6
Chemical Structure| 51639-48-6
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Product Details of [ 51639-48-6 ]

CAS No. :51639-48-6 MDL No. :MFCD00005962
Formula : C12H16N2O Boiling Point : -
Linear Structure Formula :- InChI Key :KPXVKKBJROCIJB-UHFFFAOYSA-N
M.W : 204.27 Pubchem ID :97269
Synonyms :

Safety of [ 51639-48-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51639-48-6 ]

* 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.

  • Upstream synthesis route of [ 51639-48-6 ]
  • Downstream synthetic route of [ 51639-48-6 ]

[ 51639-48-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 110-85-0 ]
  • [ 403-42-9 ]
  • [ 51639-48-6 ]
YieldReaction ConditionsOperation in experiment
75.25% With tetrabutylammomium bromide; potassium carbonate In dimethyl sulfoxide at 80℃; for 15 h; Reflux Potassium carbonate (2.99 g, 0.02 17 9 mol) was taken in round bottom flask and dried with hot gun under vacuum. Tetra-butylammonium bromide (0.045 g , 0.0014 mol) was added followed by addition of piperazine (1.54 g, 0.018 mol) dissolved in dry dimethyl suiphoxide (5 ml). Reaction mixture was stirred at 80 ° C and then 4- fluoroacetophenone (2 g, 0.0144 mol) was added and reflux was continued for 15 h at same temperature. It was then cooled to room temperature, diluted with water, filtered, filtrate was acidified with dii. HCI, extracted with ethyl acetate and aqueous layer was basified with dii. NaOH. It was then extracted with CHCI3, CHCI3 layer dried over Na2SO4 and concentrated to get pale yellow solid (2.23 g, 75.25 percent, M.P.109°C). ‘H NMR (200 MHz, CDCI3): 6 1.91 (s, IH), 2.52 (s, 3H), 2.98-3.05 (m, 4H), 3.28-3.35 (m, 41]), 6.87 (d, J = 10 Hz, 2H), 7.87 (d, J— 10 Hz, 2H).
41.25% With potassium carbonate In dimethyl sulfoxide at 190℃; for 12 h; Heating / reflux 5.0 g of 4-fluoroacetophenone (0.036195 moles), 3.11 g of piperazine (0. 036195moles), 5.21 g of potassium carbonate powder (0.037705 moles) and 25 ml dry dimethyl SULPHOXIDE (DMSO) were mixed in a three necked flask equipped with a stirrer, nitrogen inlet, condenser, calcium chloride drying TUBE/NITROGEN outlet and a temperature probe. The mixture was heated to reflux for a total of 12 hours (~190°C) under a constant flow of nitrogen gas. The mixture was then cooled to room temperature and the mixture was filtered to remove the inorganics. A further 100 ml of DMSO was used to wash out the reaction flask. The DMSO solution was then added to 100 g of ice. The mixture obtained was extracted with 3 x 75 ml of dichloromethane. The dichloromethane layers were combined and were washed with 50ML of saturated sodium chloride solution. The dichloromethane layer was then dried using anhydrous magnesium sulphate. The magnesium sulphate was removed by filtration and the dichloromethane was then removed on a rotary evaporator to yield the crude product. 30ML of water was added to the crude product and the mixture was then filtered to recover the product. The product was washed with a further 100 ml of water and then dried in a vacuum oven at 50°C for 4 hours. Product yield 3.05 g (41.25percent) of a yellow/orange solid. The product was analysed by IR, and GC-CIMS.
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5507 - 5520
[2] Patent: WO2014/132267, 2014, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2005/7637, 2005, A1, . Location in patent: Page 7-8
  • 2
  • [ 110-85-0 ]
  • [ 99-91-2 ]
  • [ 51639-48-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
  • 3
  • [ 99-92-3 ]
  • [ 334-22-5 ]
  • [ 51639-48-6 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 39, p. 6875 - 6876
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