Synthetic method 6-amino-1-hexanol

A synthesis method and hexanol technology are applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of carbamate derivatives, etc., and can solve the problems of harsh reaction conditions, potential safety hazards, difficult to meet, etc., and achieve fewer reaction steps and cost. Low, short time effect

Inactive Publication Date: 2019-10-15
SUZHOU HUADAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The main technical problem to be solved by the present invention is that the existing synthetic methods for synthesizing 6-amino-1-ethanol have harsh reaction conditions, are difficult to meet, and have defects such as potential safety hazards, and then provide a simple, convenient, safe and efficient synthesis of 6- The synthetic method of amino-1-ethanol, and can realize its industrialized production

Method used

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  • Synthetic method 6-amino-1-hexanol
  • Synthetic method 6-amino-1-hexanol
  • Synthetic method 6-amino-1-hexanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 78 g of chlorosulfonyl isocyanate and 250 ml of toluene to the reaction flask, cool to 0°C, slowly add 18 g of methanol dropwise, and stir for 30 minutes; maintain this temperature, add 112 g of triethylamine dropwise, and continue stirring for 1 hour. Add 59 grams of 1,6-hexanediol, first stir the reaction at room temperature for 30 minutes, then raise the temperature to 50°C for 2 hours.

[0027] Suction filtration, add 100 ml of concentrated hydrochloric acid to the filtrate, heat and reflux for 3 hours, cool, separate the liquid, concentrate the water phase to dryness, use solid sodium hydroxide for alkalization, extract 3 times with tetrahydrofuran, combine the organic phases, concentrate, and the remaining The product was distilled under reduced pressure, and the 70-78°C / 1-2mmHg fraction was collected to obtain 35 grams of 6-amino-1-hexanol, with a yield of 60% and a purity of 98.2%; 1 H (NMR, CDCl3): 3.59 (t, 2H), 2.69 (t, 2H), 2.23 (brs, 3H), 1.59-1.52 (m, 2...

Embodiment 2

[0029] Add 78 grams of chlorosulfonyl isocyanate and 250 milliliters of toluene to the reaction flask, cool to 10°C, slowly add 41 grams of tert-butanol dropwise, and stir for 30 minutes; maintain this temperature, add 112 grams of triethylamine dropwise, and continue stirring for 1 hour . Add 59 grams of 1,6-hexanediol, first stir the reaction at room temperature for 30 minutes, then raise the temperature to 85°C for 2 hours.

[0030] Suction filtration, add 50 milliliters of trifluoroacetic acid to the filtrate, stir at room temperature for 12 hours, then add 100 milliliters of water to fully stir, separate liquids, concentrate the water phase to dryness, use solid sodium hydroxide for alkalization, and extract 3 times with tetrahydrofuran, The organic phases were combined and concentrated, and the residue was distilled under reduced pressure, and the 70-78°C / 1-2mmHg fraction was collected to obtain 38 g of 6-amino-1-hexanol with a yield of 65% and a purity of 98.8%.

Embodiment 3

[0032] Add 78 grams of chlorosulfonyl isocyanate and 250 milliliters of toluene to the reaction flask, cool to 15°C, slowly add 60 grams of benzyl alcohol dropwise, and stir for 30 minutes; maintain this temperature, add 112 grams of triethylamine dropwise, and continue stirring for 1 hour. Add 59 grams of 1,6-hexanediol, first stir the reaction at room temperature for 30 minutes, then raise the temperature to 85°C for 2 hours.

[0033] Suction filtration, add 100 ml of 40% hydrobromic acid to the filtrate, azeotropic dehydration reaction for 4 hours, then add 50 ml of water and stir thoroughly, separate liquids, concentrate the water phase to dryness, use solid sodium hydroxide for alkalization, and extract with tetrahydrofuran Three times, the organic phases were combined and concentrated, and the residue was distilled under reduced pressure, and the 70-78°C / 1-2mmHg fraction was collected to obtain 46 grams of 6-amino-1-hexanol with a yield of 79% and a purity of 98.5%.

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Abstract

The invention discloses a synthetic method 6-amino-1-hexanol. According to the synthetic method 6-amino-1-hexanol, chlorosulphonyl isocyanate and 1, 6-hexanediol are taken as main raw materials, one-pot method is adopted to synthesize 6-amino-1-hexanol. The synthesis route comprises following steps: 1, under the catalyst effect of a tertiary amine, chlorosulphonyl isocyanate and a primary alcoholare reacted to generate a Burgess reagent, 1, 6-hexanediol is added to generate an intermediate 6-hydroxyhexyl carbamic acid; and 2, the intermediate 6-hydroxyhexyl carbamic acid synthesized in step is subjected to projecting group removing directly without separation so as to obtain target product 6-amino-1-hexanol. The synthetic method is low in cost, simple in reaction conditions, few in reaction steps, short in time, and high in purity and yield of finished product 6-amino-1-hexanol.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a synthesis method of 6-amino-1-hexanol. Background technique [0002] 6-Amino-1-hexanol, room temperature is white to pale yellow needle-like crystal or powder solid, melting point is 58-60°C, boiling point is 225°C; it is an important chemical intermediate, it contains both hydroxyl and amino Functional group, so it has the reactivity of alcohol and amine, and can be widely used in the production of medicines, pesticides, surfactants and materials. [0003] According to literature reports, the synthetic methods of 6-amino-1-hexanol include hexamethyleneimine high-temperature and high-pressure hydrolysis method, n-hexylamine chlorination hydrolysis method, 6-chlorohexyl isocyanate high-temperature and high-pressure hydrolysis method, 1,6 -High-temperature replacement method of hexanediol and 1,6-hexanediamine, 6-hydroxyhexylcyanide hydrogenatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C215/08
CPCC07C213/02C07C269/02C07C215/08C07C271/16Y02P20/55
Inventor 陆军左美娟刘明荣
Owner SUZHOU HUADAO BIOLOGICAL PHARMA
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