Method for easily preparing aryl morpholine and aryl piperidine
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A kind of technology of aryl morpholine and aryl piperidine, which is applied in the field of preparing aryl morpholine and aryl piperidine to achieve the effect of high reaction efficiency
Inactive Publication Date: 2012-07-04
EAST CHINA UNIV OF SCI & TECH
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[0006] The technical problem to be solved by the present invention is to overcome the need for complex palladium complexes and unstable, structural Complex and expensive phosphine ligands and other defects provide an economical, simple, high-yield and practical method for the preparation of arylmorpholines and arylpiperidines
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Embodiment example 1
[0020] The preparation of implementation case 1N-phenylmorpholine
[0021] Under nitrogen protection, 144mg (1.5mmol) sodium tert-butoxide, 3.6mg (0.02mmol) palladium dichloride, 10.6mg (0.04mmol) triphenylphosphine, 157mg (1.0mmol) bromobenzene were successively added to a 25ml Schlenk bottle , 130.5mg (1.5mmol) morpholine, 5.0ml toluene, heating to reflux for 5h, adding an appropriate amount of water to quench the reaction, extracting with ethyl acetate (3×10ml), combining the organic phases, concentrating, and separating by column chromatography to obtain White solid 141.7 mg, yield 88.0%. mp 49-51°C. 1 HNMR (400MHz, CDCl 3 ) δ 3.07 (t, J = 4.7Hz, 4H), 3.77 (t, J = 4.7Hz, 4H), 6.89-6.73 (m, 3H), 7.18-7.20 (m, 2H).
Embodiment 2
[0022] The preparation of embodiment 2 N-4-methylphenylmorpholine
[0023] The reaction substrate was replaced with 171 mg (1.0 mmol) of 4-methylbromobenzene, and the rest of the experimental conditions and operations were the same as in Example 1 to obtain 153.1 mg of a light yellow solid with a yield of 86.0%; mp 48-50°C. 1 H NMR (400MHz, CDCl 3 )δ2.20(s, 3H), 3.03(t, J=4.8Hz, 4H), 3.78(t, J=4.8Hz, 4H), 6.76(d, J=8.5Hz, 2H), 7.01(d, J=8.5Hz, 2H).
Embodiment example 3
[0024] Implementation Case 3 Preparation of N-4-chlorophenylmorpholine
[0025] The reaction substrate was replaced with 191.5 mg (1.0 mmol) of 4-chlorobromobenzene, and the remaining experimental conditions and operations were the same as in Example 1 to obtain 175.6 mg of a white solid with a yield of 88.9%. mp 65-68°C. 1 H NMR (400MHz, CDCl 3 )δ3.04(t, J=4.8Hz, 4H), 3.78(t, J=4.8Hz, 4H), 6.75(d, J=8.9Hz, 2H), 7.14(d, J=8.9Hz, 2H) .
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Abstract
The invention relates to a method for easily preparing aryl morpholine (formula I) and aryl piperidine (formula II). The preparation method mainly comprises the following steps of: reacting morpholine (formula III) or piperidine (formula IV) with aryl bromide (formula V) in an organic solvent in the presence of a catalytic amount of palladium compound with a simple structure, a phosphorus (phosphonium) ligand with a simple structure and an alkali at a certain temperature for 3-10 hours; and performing column chromatography isolation to obtain aryl morpholine (formula I) or aryl piperidine (formula II). Compared with the conventional method for preparing aryl morpholine and aryl piperidine, the method has the advantages of easiness, readily-available catalysts and ligands, low preparation cost, high yield and the like.
Description
technical field [0001] The invention relates to a method for simply preparing aryl morpholine and aryl piperidine, in particular to a method for preparing aryl morpholine and aryl piperidine through a simple Buchwald-Hartwig reaction. Background technique [0002] Arylmorpholine and arylpiperidine compounds are widely used in organic chemistry, medicinal chemistry, material science and other fields. It plays an increasingly important role in the synthesis of organic dyes, natural compounds, pharmaceutical intermediates, biologically active substances, and functional materials. (B.B.Sniker, et al.J.Am.Chem.Soc.1998, 120, 6417-6418; U.Scholz, et al.Adv.Synth.Catal.2004, 346, 1599-1626) [0003] The traditional method of synthesizing arylmorpholine / arylpiperidine uses copper or copper compounds as catalysts, but its reaction conditions are harsh and have many limitations, such as high temperature, equivalent catalyst, and basically only Effective against iodoarenes (J. Hassa...
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