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Chemical Structure| 61337-88-0

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Product Details of [ 61337-88-0 ]

CAS No. :61337-88-0
Formula : C17H18N4
M.W : 278.35
SMILES Code : CN1CC(C2=CC=CC=C2)N(C3=NC=CC=C3C#N)CC1
MDL No. :MFCD08669436

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* 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.

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[ 61337-88-0 ] Synthesis Path-Upstream   1~1

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YieldReaction ConditionsOperation in experiment
20.9% at 25 - 70℃; for 5 - 20 h; Example 1
One gram (1 g) of 2-(4-methyl-2-phenylpiperazin-1-yl)-3-cyanopyridine, 10 ml of an aqueous sulfuric acid solution of 50percent by weight, and 0.2 g of the catalyst produced by the preparation example of a catalyst were mixed and catalytically reduced in hydrogen at a gage pressure of 3 kgf/cm2 (294 kPa) and 70°C.
After 5 hours, the reaction liquid was analyzed by a HPLC analysis, and it was confirmed that 71.9percent of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol was produced.
Example 2; One gram (1 g) of 2-(4-methyl-2-phenylpiperazin-1-yl)-3-cyanopyridine, 5 ml of an aqueous sulfuric acid solution of 50percent by weight, and 0.2 g of the catalyst produced by the preparation example of a catalyst were mixed and catalytically reduced in hydrogen at a hydrogen gage pressure of 3 kgf/cm2 (294 kPa) and 70°C. After 5 hours, the reaction liquid was analyzed by a HPLC analysis, and it was confirmed that 68.3percent of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol was produced.; Example 3; One gram (1 g) of 2-(4-methyl-2-phenylpiperazin-1-yl)-3-cyanopyridine, 10 ml of an aqueous sulfuric acid solution of 33percent by weight, and 0.2 g of the catalyst produced by the preparation example of a catalyst were mixed and catalytically reduced in hydrogen at a gage pressure of 3 kgf/cm2 (294 kPa) and 70°C. The reaction liquid was analyzed by a HPLC analysis, and it was confirmed that 69.1percent of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol was produced. The reaction liquid was neutralized with an aqueous sodium hydroxide solution of 25percent by weight and extracted with 30 ml of toluene. The extracted organic layer was concentrated, and 0.4 g of xylene, 0.1 g of 1-butanol and 1.2 g of methanol were added thereto, and the mixture was heated up to 60°C so as to be dissolved. Then, 0.53 g of 2- (4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol was produced by adding 1.3 g of heptane to the heated dissolved liquid, cooling down to 0 to 5°C, aging for 1 hour to deposit a crystal, washing the deposited crystal with a mixture of toluene and heptane (solvent ratio was 1:1), and drying the crystal. (Yield: 52percent, Purity: 95.8percent) IR (KBr) ν = 1573, 1429, 1128. 1036, 757.8, 701 cm-1; Example 4; One gram (1 g) of 2-(4-methyl-2-phenylpiperazin-1-yl)-3-cyanopyridine, 10 ml of an aqueous sulfuric acid solution of 50percent by weight, and 0.2 g of the catalyst produced by the preparation example of a catalyst were mixed and catalytically reduced in hydrogen at a hydrogen gage pressure of 3 kgf/cm2 (294 kPa) and 25°C. After 20 hours, the reaction liquid was analyzed by a HPLC analysis, and it was confirmed that 20.9percent of 2-(4-methyl-2-phenylpiperazin-1-yl)pyridine-3-methanol was produced.
References: [1] Patent: EP1953150, 2008, A1, . Location in patent: Page/Page column 3-4.
[2] Organic Preparations and Procedures International, 2007, vol. 39, # 4, p. 399 - 402.
[3] Patent: EP1953150, 2008, A1, . Location in patent: Page/Page column 4.
[4] Patent: US2011/201804, 2011, A1, .
[5] Patent: JP2017/52704, 2017, A, .
[6] Patent: JP2017/218411, 2017, A, .
[7] Patent: JP2015/174853, 2015, A, .
 

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