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Chemical Structure| 918344-20-4 Chemical Structure| 918344-20-4

Structure of 918344-20-4

Chemical Structure| 918344-20-4

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Product Details of [ 918344-20-4 ]

CAS No. :918344-20-4
Formula : C14H17NO2
M.W : 231.29
SMILES Code : N#CC(C1(O)CCCCC1)C2=CC=C(O)C=C2
MDL No. :MFCD16251407

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Application In Synthesis of [ 918344-20-4 ]

* 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 [ 918344-20-4 ]

[ 918344-20-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 918344-20-4 ]
  • [ 124-40-3 ]
  • [ 539-15-1 ]
  • [ 93413-62-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium on activated charcoal; In ethanol; water; at 50℃; under 3750.38 Torr; for 10h;Product distribution / selectivity; Example 9 (Comparative example); Process for the preparation of 1-[2-(dimethylamino)-1-(4- hydroxyphenyl)ethyl]-cyclohexanol [of the general formula (I), wherein R stands for a hydrogen atom (desvenlafaxine)]; Example 1 is repeated with the exception that instead of tetrahydrofurane ethanol is used. Furthermore, a 60% aqueous solution of dimethylamine is used as dimethylamine source. <n="27"/>The product is a mixture with a composition as follows (based on HPLC measurements):12 % of 1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]- cyclohexanol, and85 % 4-[2-(dimethylamino)-ethyl]-phenol.The products are separated, purified and their chemical structures are identified. Spectral data of the separated compound of the formula 1-[2-(dimethylamino)-1-(4- hydroxyphenyl)ethyl]-cyclohexanol correspond to the data of the product of Example 1. The melting point and spectral data of the separated compound of the formula 4-[2-(dimethylamino)-ethyl]-phenol correspond to the data of the prior art (Tetrahedron 1990, 46, 7105).; Example 1; Process for the preparation of 1-[2-(dimethylamino)-1-(4- hydroxyphenyl)ethyl]-cyclohexanol [of the general formula (I), wherein R stands for a hydrogen atom (desvenlafaxine)]; In a pressure-tight vessel, 6.9 g (0.03 mol) of 1-[cyano-(4- hydroxyphenyl)methyl]-cyclohexanol are suspended in 100 ml of tetrahydrofurane, then a mixture of 9.5 g (0.21 mol) of dimethylamine and 60 ml of tetrahydrofurane and 2.5 g of palladium on charcoal catalyst is added. The vessel is purged twice with nitrogen, twice with hydrogen, then the reaction mixture is kept at 50 C and hydrogenated under a pressure of 5 bar hydrogen for 10 hours, until the decrease of hydrogen pressure is stopped. The reaction mixture is cooled to room temperature, the catalyst is filtered off and washed with tetrahydrofurane. The filtrate and the washing solvent are united and evaporated in vacuo. The residue, the crude product is suspended with 30 ml of tert butyl methyl ether, filtered, washed and dried. Thus 5.5 g (70%) of title product are obtained.Melting point: 223-225 0C.IR (KBr): 3425, 2939, 1517, 1272, 843 cm"1.1H-NMR (DMSO-de, 500 MHz): 9.11 (br s, 1 H), 6.96 (d, J=8.6 Hz, 2H), 6.63 (d, J=8.6 Hz1 2H), 5.40 (br s, 1H)1 2.99 (m, 1H), 2.71 (m, 1H), 2.34 (m, 1H)1 2.14 (s, 6H)1 0.8-1.6 (m, 10H) ppm. <n="23"/>13C-NMR (DMSO-de, 125 MHz): 155.7, 131.9, 130.2, 114.6, 72.7, 60.6, 51.8, 45.5, 37.3, 32.6, 25.9, 21.5, 21.4 ppm.Elementary analysis based on the formula C16H25NO2:Calculated: C % = 72.97; H % = 9.57; N % = 5.32 Measured: C % = 72.80; H % = 9.64; N % = 5.19.
 

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