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Method for preparing N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride

A technology of methyl ethyl and methanesulfonamide, applied in the field of preparing N-[4-[1-hydroxyl-2-[(1-methylethyl)amino]ethyl]methanesulfonamide hydrochloride , can solve the problems of low total yield, long steps, and low yield of key reactions, and achieve the effect of convenient purification, short steps, and cost reduction

Active Publication Date: 2012-01-25
SHANGHAI AOBO PHARMTECH INC LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology uses less expensive or easier-to-produce starting material like aminobenzene sulfonate with strong bases at room temperature to make it difficult to break down into smaller molecules during chemical synthesis without losing its desired properties. It also allows for direct preparation of specific products from these reactants without any extra process steps needed beforehand. These technical results help reduce costs while maintaining good quality final products made up mostly of pure components.

Problems solved by technology

Technological Problem addressed in this patents relates to improving the efficiency and effectiveness of producing drugs called sunitimod or selvedoxyfrasonic acid through methods like chemosynthesis involving reactions between different molecules such as intermediators, solvent bases, reducing agents, etc. These improvements can lead to lower costs associated with manufacturing processes while maintaining their quality and efficacy.

Method used

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  • Method for preparing N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride
  • Method for preparing N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride
  • Method for preparing N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride

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Embodiment 1

[0044] The synthesis of embodiment one N-phenylmethanesulfonamide (II)

[0045] 50 g of aniline was dissolved in 500 ml of dichloromethane, and 60 g of triethylamine was added. Under an ice bath, 68 g of methanesulfonyl chloride was added dropwise to the system. It was subsequently stirred at room temperature for 3 hours.

[0046] Under an ice bath, 500 ml of 10% sodium hydroxide aqueous solution was slowly added dropwise to the reaction solution, and after fully stirring, the water layer was separated. The aqueous layer was adjusted to pH=1 with concentrated hydrochloric acid. At this time, a large amount of white solid was precipitated, filtered and dried to obtain 90 g of a solid product with a yield of 97% and a purity of 99.1%.

Embodiment 2

[0047] The synthesis of embodiment two N-[4-[2-chloroacetylphenyl] methanesulfonamide (III)

[0048] Under ice-cooling, 90 g of N-phenylmethanesulfonamide (II) was dissolved in 500 ml of dichloromethane, and then 95 g of aluminum trichloride and 70 g of chloroacetyl chloride were added. Keep this temperature for 6 hours.

[0049] The reaction solution was poured into cold aqueous hydrochloric acid, and a large amount of white solid was precipitated. After filtering and drying, 120 g of the product was obtained as a solid, with a yield of 92% and a purity of 99.8%.

Embodiment 3

[0050] Synthesis of Example Three N-[4-[2-(1-methylethyl)amino]acetyl]methanesulfonamide hydrochloride (IV)

[0051] 120 g of N-[4-[2-chloroacetylphenyl]methanesulfonamide (III), 39 g of sodium hydroxide, and 114 g of isopropylamine were added to 500 ml of triethylamine, and stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, and 1L of saturated ethanol hydrochloric acid was added to the resulting mixture. A large amount of white solid precipitated out. The white solid was filtered, washed with absolute ethanol, and dried to obtain compound (IV), which contained some inorganic salts. This mixture can be directly used for the next reaction without purification.

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Abstract

The invention discloses a novel method for preparing N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride (I), which comprises: reaction of phenylamine and methanesulfonyl chloride to produce N-phenyl methanesulfonamide (II), reaction of the obtained compound (II) and chloroacetyl chloride to produce N-[4-[2-chloroacetyl phenyl]methanesulfonamide (III), reaction of the obtained compound (III) and isopropamide to produce N-[4-[2-(1-methylethyl)amino]acetyl]methylsulfonyl benzylamine hydrochloride (VI), and reduction of the obtained compound (VI) by sodium borohydride to produce the target product N-[4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]methylsulfonyl benzylamine hydrochloride (I). The method has the advantages of low cost, short reaction procedures, simple operation, high yield, high product purity and the like, and is suitable for industrial production.

Description

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Claims

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Application Information

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Owner SHANGHAI AOBO PHARMTECH INC LTD
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