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Process for preparation of phenethylamine derivatives

A technology for compounds and composites, applied in the field of preparing phenethylamine derivatives, can solve problems such as being difficult to separate final products

Inactive Publication Date: 2006-04-05
WYETH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The physical and chemical properties of the phenethylamine impurity are very similar to the desired end product primary amine, therefore, it is difficult to separate it from the desired end product

Method used

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  • Process for preparation of phenethylamine derivatives
  • Process for preparation of phenethylamine derivatives
  • Process for preparation of phenethylamine derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 25.0 g of Raney nickel (Kawaken, Grace 2400, 2724, Degussa B111W, 112W) and 250 ml of methanol and 25 ml of ammonia solution (25% NH 3 ). To the mixture was added 50 g of 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol, followed by 250 ml of MeOH. Fix the reactor and fill it with N 2 Gas purge two or three times. In use N 2 After thorough cleaning, use H 2 Gas purges the reactor two or three times. The internal pressure of the reactor was adjusted to 60 psi and the reaction mixture was stirred. After 20 to 30 hours of reaction at room temperature (approximately 10 to 20° C.), an in-process analysis of a sample of the mixture was performed. After the reaction was complete the Raney nickel was removed by filtration through a pad of celite. The filtrate was distilled under reduced pressure until all the solvent was evaporated, and 200 ml of isopropanol and 400 ml of ethyl acetate were added to the residual oil to dissolve the resulting product, resulting in a clear or ...

Embodiment 2 to 10

[0047] Tests were performed in the same manner as in Example 1, except that the amounts of raw materials, Raney nickel, and ammonia solution; reaction temperature; and reaction time were shown in the table below. The purity and yield of the desired product (r.t. = room temperature from about 10 to 20° C.) is also indicated in the last column of the table.

[0048] Example

Embodiment 11

[0050] Add 40ml of H into a graduated cylinder (mass cylinder) 2 After O, place the graduated cylinder on the balance. Then return the balance to zero. Add Raney nickel to the vector cylinder and remove the increased volume of water, maintaining a total volume of 40ml, until the balance shows a total weight of 12g. Remove H 2 O and add 40g fresh H 2 O, to wash the catalyst. After washing, the removal of H 2 O. Add Raney nickel to the reactor, while using 20ml of H 2 O and 600 MeOH rinse. To the mixture was added 40 g of 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol, followed by 20 ml of ammonia solution. The reactor was fixed and then filled with N 2 Gas purge two or three times. In use N 2 After adequate purging, the reactor was purged two or three times with hydrogen. The internal pressure of the reactor was adjusted to 60 psi, and stirring was started. After 20 to 30 hours of reaction at room temperature, an in-process analysis of a sample of the mixture was per...

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PUM

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Abstract

A process for the preparation of a compound of formula (I), wherein R1, and R2 are ortho or para substituents, independently selected from the group consisting of hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy, C7-C9 aralkoxy, C2-C7 alkanoyloxy, C1-C6 alkylmercapto, halo and trifluoromethyl; R3 is hydrogen or C1-C6 alkyl; R4 is hydrogen, C1-C6 alkyl, formyl or C2-C7 alkanoyl; n is one of the integers 0, 1, 2, 3 or 4; and the dotted line represents optional olefinic unsaturation; comprising hydrogenating a compound of formula (III), in the presence of a nickel or cobalt catalyst at a temperature of about 5 DEG C to 25 DEG C.

Description

technical field [0001] The present invention relates to an improved process for the preparation of phenethylamine derivatives by hydrogenation of benzyl nitrile in the presence of nickel or cobalt catalysts. Background technique [0002] Compounds of formula I are useful intermediates for the preparation of pharmaceutically active substances which have central nervous system antidepressant effects by inhibiting the reuptake of neurotransmitters, norepinephrine and serotonin. An example of such an antidepressant is Venlafaxine (see Merk Index Twelfth Edition 1996, No. 10079). As disclosed in US Patent 4,535,186, compounds of formula I can be prepared by coupling a cycloalkanone or cycloalkenone with an appropriately substituted benzylnitrile (step 1), followed by catalytic hydrogenation of the coupled benzylnitrile (step 2). The present invention relates to the improvement of the second step reaction. [0003] According to the preparation method disclosed in US Patent 4,535...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C217/14C07C215/42C07C217/74
CPCC07C213/02C07C2101/14A61P25/24A61P43/00C07C2601/14C07C215/42C07C217/74C07C213/10
Inventor K·-S·金K·-I·金K·-B·蔡
Owner WYETH LLC
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