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Process for producing benzylamine compound

A manufacturing method and compound technology, applied in organic chemistry and other fields, can solve the problems of many steps and complicated operation, and achieve the effect of good operability and good economy

Inactive Publication Date: 2002-12-25
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Above-mentioned manufacturing method has many steps, and operation is also loaded down with trivial details

Method used

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  • Process for producing benzylamine compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Method for producing compound (2) using dl-valine in N,N-dimethylacetamide (case where low boiling point substances are not evaporated.)

[0039] In a 20 ml reaction vessel, add 1 g of the monohydrochloride salt of compound (1), 0.58 g of dl-valine, 6 g of N,N-dimethylacetamide and 2.5 ml of 1 mol / L hydrochloric acid-diox The alkane solution was stirred at an internal temperature of 150°C for 2 hours.

[0040] After cooling the reaction mixture to 40°C, 20 mg of seed crystals were added to precipitate crystals, and then the internal temperature was cooled to 10°C and maintained at this temperature for 1 hour.

[0041] Thereafter, the crystals were filtered and washed with 1 g of diisopropyl ether to obtain 0.74 g of dihydrochloride of benzylamine compound (2).

[0042] Melting point: 262°C (decomposition)

Embodiment 2

[0044] Method for producing compound (2) using 2-aminoisobutyric acid in N,N dimethylacetamide (case where low boiling point substances are not distilled off.)

[0045] In a 20 ml reaction vessel, add 200 mg of the monohydrochloride salt of compound (1), 57 mg of 2-aminoisobutyric acid, 1.2 g of N,N-dimethylacetamide and 0.2 g of 10% (w / w) Hydrochloric acid-ethanol solution was stirred at an internal temperature of 150°C for 2 hours.

[0046] The reaction mixture was cooled until crystallization occurred (ca. 40°C), then the internal temperature was allowed to cool to 10°C and held at this temperature for 1 hour.

[0047] Thereafter, the crystals were filtered and washed with 1 g of diisopropyl ether to obtain 0.16 g (yield 73%) of dihydrochloride of benzylamine compound (2).

[0048] Melting point: 262°C (decomposition)

Embodiment 3

[0050] Method for producing compound (2) using dl-valine in N,N-dimethylacetamide (case of evaporating low-boiling point substances.)

[0051] In a 100 ml reaction vessel, add 7 gram of compound (1) monohydrochloride, 3.04 gram of dl-valine, 28.89 gram of N,N-dimethylacetamide and 1.35% concentrated hydrochloric acid, at 110 The mixture was stirred for 2 hours while distilling off low boiling point substances at an internal temperature of -120°C.

[0052] 6.45 g of N,N-dimethylacetamide was distilled off under reduced pressure, and when the internal temperature was 75°C, 10.5 g of isopropyl ether was added, the internal temperature was cooled to 5°C, and this temperature was maintained for 1 hour.

[0053] The precipitated crystals were filtered and washed with a mixed solvent of 3.3 g of N,N-dimethylacetamide and 3.3 g of isopropyl ether to obtain 5 g of dihydrochloride of benzylamine compound (2).

[0054] Melting point: 262°C (decomposition)

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Abstract

A process for producing a benzylamine compound represented by formula (2), which comprises reacting a benzaldehyde compound represented by formula (1) with an amino acid in the presence of an acid. <CHEM> <CHEM>

Description

technical field [0001] The present invention relates to a novel production method of a benzylamine compound which is an important intermediate of the following pyridazinone compound (3) used in pharmaceuticals. Background technique [0002] WO95 / 01343 and JP-A-8-041033 disclose that the pyridazinone compound (3) is a useful compound as a medicine having bronchodilator action, antiallergic action, antiplatelet action, and the like. [0003] Compound (2) is an important synthetic intermediate of pyridazinone compound (3), which is prepared from isovanillin (4) as a reaction raw material according to the following reaction formula. [0004] The above-mentioned manufacturing method has many steps, and the operation is also complicated. [0005] In particular, the use of benzyloxycarbonyl (Z) as a protecting group requires not only two additional steps of insertion and detachment, but also expensive reagents such as benzyloxycarbonyl chloride (ZCl), so from the viewpoint of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/182C07D295/185
CPCC07D295/182C07D295/185
Inventor 清水孝纪河原史郎堀内贵
Owner NISSAN CHEM IND LTD
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