Nippon Soda Co., Ltd.

Tsutomu Imagawa

Yasushi Shibata

Hirohito Oooka

Hiroki Inoue

Shinya Fukuhara

Hiroshi Hakuta

Mutsumi Sugawara

Fumitaka Masui

The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid. (wherein A represents an organic group, R represents a hydrogen atom, or an organic group, L represents a halogen atom and the like, and n represents an integer of 2 to 20).

Process for producing substituted methylamine compound and triazine derivative

The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid. (wherein A represents an organic group that is either a hydrocarbon group or a heterocyclic group, or said organic group that has a substituent, R represents a hydrogen atom, an organic group that is either a hydrocarbon group or a heterocyclic group, or said organic group that has a substituent, L represents a halogen atom and the like, and n represents an integer of 2 to 20)

There are provided, according to the present invention, a method for producing a cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative, the method characterized in that a trans-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative or a mixture of the trans- and cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivatives is isomerized in the presence of an aluminum compound represented by a formula Al(OR)(wherein Rrepresents a hydrocarbon group in which a carbon atom having an oxygen atom bonded thereto is a secondary carbon atom). In the process, a ketone compound may be further added, in addition to the aluminum compound.

Method for producing cis-3-substituted-3-azabicyclo[3.2.1]octan-8-ol derivative

Provided is a method for producing a piperidin-4-one derivative useful as an intermediate for agricultural chemicals or pharmaceutical products. A piperidin-4-one derivative represented by formula (III-a) or formula (III-b) is produced by reacting a cyclic bis(aminol)ether compound represented by formula (I) and an acetone derivative represented by formula (II) in the presence of at least one substance selected from the group consisting of protonic acids, Lewis acids, acid halides and dialkyl sulfuric acids.

Method for producing piperidin-4-one derivative

A method for producing chlorosulfonyl isocyanate by reaction of sulfur trioxide with cyanogen chloride, wherein chlorosulfonyl isocyanate or a solution including chlorosulfonyl isocyanate is used as a reaction solvent, sulfur trioxide and cyanogen chloride which are respectively diluted with the chlorosulfonyl isocyanate or the solution including chlorosulfonyl isocyanate are added at the same time to a reaction system in an almost equimolar amount under reflux. By the production method of present invention, chlorosulfonyl isocyanate can be produced from sulfur trioxide and cyanogen chloride in which the yield of the chlorosulfonyl isocyanate is high, the method has excellent operability, number of equipments is reduced, and time for controlling the temperature is saved.

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Takaoka, Japan

Tsutomu Imagawa