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Chemical Structure| 58258-01-8 Chemical Structure| 58258-01-8

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Chemical Structure| 58258-01-8

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Product Details of [ 58258-01-8 ]

CAS No. :58258-01-8
Formula : C18H21NO
M.W : 267.37
SMILES Code : C1(OC(C2=CC=CC=C2)C3=CC=CC=C3)CCNCC1
MDL No. :MFCD06659472

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Application In Synthesis of [ 58258-01-8 ]

* 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 [ 58258-01-8 ]
  • Downstream synthetic route of [ 58258-01-8 ]

[ 58258-01-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 58258-01-8 ]
  • [ 43076-61-5 ]
  • [ 90729-43-4 ]
YieldReaction ConditionsOperation in experiment
66.43% With sodium hydrogencarbonate In toluene for 12 h; Reflux Example 3. Preparation of discoloured l-[4-(l,l-dimethyIethyl)phenyI]-4-[4- (diphenylmethoxy)-l-piperidinyl]-l-butanone I"A toluene solution of 4-benzhydryloxypiperidine (73.27 g of the toluene solution contained 26.74 g of 4-benzhydryloxypiperidine), sodium hydrogen carbonate (14.28 g), DMF (5.3 mL) and 4'-tert-butyl-4-chloro-butyrophenone (28.65 g) were heated to reflux temperature. The reaction mixture was heated at reflux temperature for 12 h, to produce a solution of I" of 84.3percent) purity on the basis of HPLC area-percent and then cooled to room temperature. The orange reaction mixture was washed with water (3 x 100 mL) and the organic phase wasconcentrated under reduced pressure. Ethanol (110 mL) was added to the residue and the mixture was heated to reflux. The hot solution was filtered and the filtrate was cooled to 2 °C. The product was isolated by filtration and washed with ethanol (5 x 20 mL). The product was dried in a vacuum oven for several hours to afford the title compound (31.2 g, 66.43 percent) as a beige solid (commercial I" is white and specifications (such as those found in the European Pharmacopoeia) require a white to almost white crystalline substance). HPLC purity 99.77 percent, significant impurities at relative retention times 0.05 and 0.19 were observed and had HPLC area-percent of 0.04 and 0.06percent>. Discolouration was also sometimes observed when other solvents, including methyl isobutyl ketone were used, but was able to be efficiently suppressed when air was excluded from the reaction mixture, or was able to be efficiently suppressed when an adequate purification procedure by salt formation/neutralization, alternatively or optionally in combination with recrystallization, was used.
References: [1] Patent: WO2011/121099, 2011, A2, . Location in patent: Page/Page column 40-41.
[2] Patent: EP2371817, 2011, A1, . Location in patent: Page/Page column 28.
 

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