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Process for preparing N-(substituted arylmethyl)-4-substituted-4- (disubstituted methyl) piperidines and intermediates

An intermediate and two-substituted technology, applied in the field of chemistry, can solve the problems of suboptimal yield, suboptimal cycle time, high catalyst loading, etc.

Inactive Publication Date: 2007-08-15
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disadvantages of the process disclosed in WO2005 / 036961 for the production of these compounds include: suboptimal yields, strong exothermic reactions due to the presence of fluorine, suboptimal cycle times and high catalyst loadings

Method used

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  • Process for preparing N-(substituted arylmethyl)-4-substituted-4- (disubstituted methyl) piperidines and intermediates
  • Process for preparing N-(substituted arylmethyl)-4-substituted-4- (disubstituted methyl) piperidines and intermediates
  • Process for preparing N-(substituted arylmethyl)-4-substituted-4- (disubstituted methyl) piperidines and intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0174]

[0175] Embodiment 1 (continued)

[0176]

[0177] a-i)THF / I-PrMgCl / 15°C to room temperature / 24h a-ii)HCO 2 Et / -10~0℃a-iii)10%NH 4 Cl b) octane / HBr / acetic acid / room temperature / 3h c-i) tert-butyllithium / THF / -85~-60℃ / 12h c-ii) HCl(g) d)MeOH / HCOOH / 'Pd(OH) 2 / C' / 40~55℃ / 4h e)K 2 CO 3 / Cu 2 O / 145~170℃ / 3.5h g)THF / NaBH(OAc) 3 / room temperature / 12h h)50%H 2 o 2 / MeOH / 40~55℃ / 9-44h

[0178] As shown in Example 1, in the first step, two molecules of a substituted aryl halide, for example, the known compound 4-bromo-1-(trifluoromethoxy)benzene (A), and a Reaction of Riya reagent with an alkyl formate, eg, ethyl formate, forms bis[4-(trifluoromethoxy)phenyl]methanol-1 (B). Afterwards, intermediate (B) reacts with hydrogen bromide under acidic conditions to generate the corresponding (4-(bromo[4-(trifluoromethoxy)phenyl]methyl)phenoxy)trifluoromethane (c) . Intermediate (c) is then lithiated, for example with butyl lithium, and then reacted with a suitable N-subst...

Embodiment 2

[0180] The process of generating (F) from steps a) to d) is the same as in Example 1.

[0181] Example 2

[0182]

[0183] Embodiment 2 (continued)

[0184]

[0185] e)K 2 CO 3 / Cu 2 O / 145~170℃ / 3.5h f)Br 2 j) K 2 CO 3 / DMF h)50%H 2 o 2 / MeOH / 40~55℃ / 9-44h

[0186]Example 2 In the first step, a suitable substituted phenol, such as the known compound 4-methylphenol, and a halogenated pyridine, such as 2-chloropyridine, can be oxidized in potassium carbonate and a catalytic amount In the presence of copper, react at a temperature of 145-170°C to form 2-(4-methylphenoxy)pyridine (G2). Intermediate (G2) can then be halogenated using eg bromine to form 2-[4-(bromomethyl)phenoxy]pyridine (H). In the presence of potassium carbonate, intermediate (F) as prepared in Example 1 can react with intermediate (H) to form 4-{bis[4-(trifluoromethoxy)phenyl]methyl}-1 -[(4-(2-Pyridyloxy)phenyl)methyl]piperidin-4-ol (J). Intermediate (J) can then be oxidized as in Example 1 ...

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Abstract

Disclosed are an improved process for preparing a N-(substituted arylmethyl)4-substituted-4-(disubstituted methyl)piperidine of formula (I): wherein R<1> and R<2> are independently selected from the group consisting of halogen, CF3, OCF3, OCHF2, OCF2CHF2 and SF5; and Z and B are independently selected from the group consisting of CH and N; and a method for preparing an intermediate for the improved process.

Description

[0001] This application claims priority to US Provisional Application 60 / 609,533, filed September 13,2004. technical field [0002] The invention belongs to the field of chemical methods; more specifically, an improved method for preparing N-(substituted arylmethyl)-4-substituted-4-(disubstituted methyl)piperidines, and intermediates used in the method method and novel intermediates for this method. Background technique [0003] N-(substituted arylmethyl)-4-substituted-4-(disubstituted methyl)piperidines are useful insecticides and are described in PCT published patent application WO2005 / 036961, the contents of which are incorporated by reference incorporated into this manual. Disadvantages of the process for producing these compounds disclosed in WO2005 / 036961 include suboptimal yields, strong exothermic reactions due to the presence of fluorine, suboptimal cycle times and high catalyst loadings. The present invention improves yield, cycle time and catalyst loading, and m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10A61K31/4747C07D211/40
CPCC07D401/12C07D211/46A61K31/445A61K31/47C07D211/48
Inventor J·古达D·S·罗森W·H·伊格尔王国志张群R·佩特若
Owner BAYER CROPSCIENCE AG