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Chemical Structure| 4492-37-9 Chemical Structure| 4492-37-9

Structure of 4492-37-9

Chemical Structure| 4492-37-9

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Product Details of [ 4492-37-9 ]

CAS No. :4492-37-9
Formula : C8H17N
M.W : 127.23
SMILES Code : CCNCC1CCCC1

Safety of [ 4492-37-9 ]

Application In Synthesis of [ 4492-37-9 ]

* 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 [ 4492-37-9 ]

[ 4492-37-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 26820-34-8 ]
  • [ 4492-37-9 ]
  • [ 956631-79-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In toluene; at 110℃; for 3.0h; Example N: Preparation of {5-[N-(cyclopentylmethyl)-N-ethylamino]-1 -methyl- 7H-pyrrolo[3,2- b]pyridin-6-yl}methanol <n="102"/>al,Step 1 :A mixture of <strong>[26820-34-8]2-chloro-6-methyl-5-nitronicotinonitrile</strong> (997 mg, 5.05 mmol), N- (cyclopentylmethy)-N-ethylamine (770 mg, 6.05 mmol), and K2CO3 (1.7 g, 12.3 mmol) in toluene (20 mL) is heated to 110 0C. After stirring for 3 hours, the reaction mixture is filtered to remove the resulting precipitate. The filtrate is diluted with EtOAc and washed with H2O and brine. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica-gel column chromatography to give 2-[N-(cyclopentylmethyl)-N- ethylamino]-6-methyl-5-nitronicotinonitrile as orange oil.1H-NMR (400MHz, CDCI3), delta (ppm): 1.30 (t, 3H), 1.22-1.33 (m, 2H), 1.55-1.64 (m, 2H), 1.65- 1.76 (m, 2H), 1.75-1.85 (m, 2H), 2.32 (ddt, 1 H), 2.78 (s, 3H), 3.77 (d, 2H), 3.88 (dd, 2H), 8.54 (s, 1 H).
  • 2
  • [ 51171-02-9 ]
  • [ 4492-37-9 ]
  • [ 898911-70-1 ]
YieldReaction ConditionsOperation in experiment
43% With potassium carbonate; In N,N-dimethyl-formamide;Heating / reflux; Step (ii): Synthesis of 2-(cyclopentylmethyl-ethyl-amino)-pyrazine-2-carboxylic acid methyl ester; 3-Bromo-pyrazine-2-carboxylic acid methyl ester (0.893 g, 4.11 mmol), obtained from a scale-up reaction of step (i), and potassium carbonate (1.7 g, 12.3 mmol) were added to a 50 mL two neck round bottom flask. To this flask, 10 mL of DMF was added, followed by the dropwise addition of a DMF solution of N-cyclopentylmethyl ethyl amine (0.627 g, 4.93 mmol). This mixture was refluxed overnight, after which it was allowed to cool to RT, poured onto crushed ice (10 mL), and extracted with ethyl acetate (3 x 50 mL). The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated under vacuum to give the title compound (0.468 g), yield: 43%. 1H NMR (CDCl3, 400 MHz): d 8.11 (m, IH), 7.87 (m, IH), 3.96 (s, 3H), 3.46-3.39 (m, 4H), 2.29-2.25 (m, IH), 1.71-1.60 (m, 3H), 1.19-1.15 (m, 3H), 0.88-0.83 (m, 5H) m/z (CI-MS): 264 (M+H-I, 100%); IR (cm-1): 3749, 3421, 2951.
  • 3
  • [ 4492-37-9 ]
  • [ 146137-78-2 ]
  • [ 1029317-36-9 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate; In toluene; for 68h;Heating / reflux; To a solution of 2-fluoro-5-(trifluoromethyl)benzaldehyde (3.00 g, 15.6 mmol) in toluene (60 mL) was added N-(cyclopentylmethyl)-N-ethylamine (2.70 g, 21.2 mmol) synthesized by the method described in International Patent Publication WO2006/073973 and potassium carbonate (6.50 g, 47.0 mmol), and the mixture was refluxed by heating for 68 hours. The reaction mixture was cooled to room temperature, then added with water, and extracted with chloroform. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 2-[(cyclopentylmethyl)(ethyl)amino]-5-(trifluoromethyl)benzaldehyde (3.34 g, 71%) as a yellow oil.1H-NMR (CDCl3) δ: 1.09-1.19 (5H, m), 1.43-1.72 (6H, m), 2.15 (1H, m), 3.17 (2H, d, J=7.6 Hz), 3.33 (2H, q, J=7.0 Hz), 7.19 (1H, d, J=9.0 Hz), 7.65 (1H, dd, J=2.4, 9.0 Hz), 8.03 (1H, d, J=2.4 Hz), 10.18 (1H, s).
 

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