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Technique for preparing N-substituted morpholines organic compounds

An organic compound and preparation process technology, applied in the direction of organic chemistry, etc., can solve the problems of high price of toluene as a solvent, low flash point of toluene, unsuitable for amplification, etc., and achieve obvious cost and technical advantages, low price and stable yield. Effect

Active Publication Date: 2011-05-04
BIOCOMPOUNDS PHARMACEUTICAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(PCT Int.Appl.2004024703, 25 Mar 2004.) Moreover, the price of toluene as a solvent in this method is high, and toluene has a low flash point and is dangerous, so it is not suitable for scale-up

Method used

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  • Technique for preparing N-substituted morpholines organic compounds
  • Technique for preparing N-substituted morpholines organic compounds
  • Technique for preparing N-substituted morpholines organic compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a 250ml three-necked flask, add morpholine (10.5g, 0.12mol), sodium hydroxide (4.80g, 0.12mol), bromoethane (13.8g, 0.12mol), potassium iodide (1.0g, 6mmol), acetone (30ml ) and a stirrer, stirred and reacted under reflux at 56° C. for 5 hours. Stop the reaction and filter. The filter cake was washed with acetone, the filtrates were combined, and the acetone was evaporated. Add 60ml of dichloromethane, wash once with 20ml saturated sodium bicarbonate solution, and once with 20ml saturated brine. Dichloromethane was distilled off to obtain 14 g of a pale yellow liquid. It was distilled under reduced pressure, and the fraction at 68°C was collected to obtain a colorless liquid (8.4 g, yield 60.5%). 1H-NMR (TMS, CDCl3) δ 3.73 (t, J = 7.0Hz, 4H), 2.44 (t, J = 6.8Hz, 4H), 2.41 (m, 2H), 1.09 (t, 3H).

[0031] Product Molecular Formula:

[0032]

Embodiment 2

[0034] In a 250ml three-necked flask, add morpholine (10.5g, 0.12mol), sodium hydride (2.88g, 0.12mol), 1-chloro-3-bromopropane (18.9g, 0.12mol), sodium bromide (0.12g, 1.2mmol), chloroform (60ml) and a stirrer, stirred and reacted under reflux at 61°C for 12 hours. Stop the reaction and filter. The filter cake was washed with chloroform, the filtrates were combined, and the chloroform was distilled off. Add 60ml of dichloromethane, wash once with 20ml saturated sodium bicarbonate solution, and once with 20ml saturated brine. Dichloromethane was distilled off to obtain 22 g of a yellow liquid. Distilled under reduced pressure, collected fractions at 80°C to obtain light yellow liquid (12.3 g, yield 63.0%). 1H-NMR (TMS, CDCl 3 ) δ 3.70 (t, j = 6.5 Hz, 4H), 3.61 (t, J = 6.5 Hz, 2H), 2.47 (m, 6H), 1.95 (m, 2H). Product Molecular Formula:

[0035]

Embodiment 3

[0037] In a 250ml three-necked flask, add morpholine (10.5g, 0.12mol), potassium carbonate (16.6g, 0.12mmol), allyl bromide (14.5g, 0.12mol), potassium bromide (0.29g, 2.4mmol), Methyl tert-butyl ether (150ml) and a stir bar were stirred at 0°C for 8 hours. Stop the reaction, filter, wash the solid with methyl tert-butyl ether, evaporate the combined filtrate to remove methyl tert-butyl ether, add 60ml of dichloromethane, wash once with 20ml saturated sodium bicarbonate solution, and once with 20ml saturated brine. Dichloromethane was distilled off to obtain 17.7 g of a pale yellow liquid. Distilled under reduced pressure, collected fractions at 72°C to obtain light yellow liquid (11.3 g, yield 73.9%). 1H-NMR (TMS, CDCl 3 )δ5.83 (m, 1H), 5.18 (d, 1H), 5.15 (s, 1H), 3.72 (t, 4H), 2.99 (d, 2H) 2.45 (t, 4H) product molecular formula:

[0038]

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PUM

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Abstract

The invention relates to a preparation process of N substituted morpholines organic compound, and discloses a preparation process of N substituted morpholines organic compound, which comprises adding equal molar weight morpholine, halogenated hydrocarbon and alkalinizing agent and alkali halide whose molar weight is 1%-10% of morpholine in organic solvent to obtain reaction solution, reacting to generate N substituted morpholines organic compound, and purifying N substituted morpholines organic compound to obtain purity product of N substituted morpholines organic compound. The process which is provided by the invention has mild reaction condition, simple operation, high safety and easy industrialization, yield stably reaches over 60%, the cost of agent is low, and the agent is easy to access. The invention has significant cost and technical advantages.

Description

technical field [0001] The invention relates to a preparation process of N-substituted morpholine organic compounds. Background technique [0002] N-substituted morpholine organic compounds can be prepared by the following two routes: [0003] Route 1: As shown in Figure 1, ammonia or substituted amino compounds, such as 3-aminopropanol, etc., synthesize morpholine rings with dichlorodiethyl ether. If substituted compounds such as N-bromopropyl, chloropropyl or allyl are to be prepared, a substitution reaction needs to be carried out at the alcoholic hydroxyl group (as shown in Figure 2). Therefore, the one-step reaction of this method can only prepare a few compounds such as N-alkyl, hydroxypropyl substituted morpholine, etc., which does not have universality. If the target product needs to introduce halogen atoms, two steps of reaction are required, and the required ammonia raw materials are particularly difficult to obtain, and the reaction yield is low. The final prod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/02C07D295/04
CPCC07D295/067C07D295/02C07D295/092
Inventor 李峰李倩孙婧康立涛
Owner BIOCOMPOUNDS PHARMACEUTICAL INC
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