Preparation method for fatty acyl amide

A fatty amide and aliphatic-based technology, applied in the field of organic chemical synthesis, can solve the problems of limited substrate applicability, low reaction economy, low atom economy, etc., and achieves wide substrate applicability and clean reaction process. , the effect of reducing the cost of synthesis

Active Publication Date: 2015-09-23
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

For example: method one, although the reaction is efficient, but the reaction requires a halogenated substance as a substrate, and the reaction economy is not high; method two, although the reaction is relatively novel, the substrate is only suitable for aryl toluene compounds, and an equivalent amount of The oxidant triggers the reaction, which severely limits the expansion of the reaction substrate; method 3, although the reaction is relatively new, the substrate range is only applicable to aromatic amine compounds, so the scope of substrate applicability is severely limited
Although this type of metal-catalyzed method is much improved compared with previous reactions, it still requires high temperature and high pressure, equivalent additives, and the atom economy is not high

Method used

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  • Preparation method for fatty acyl amide

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Experimental program
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Effect test

Embodiment 1

[0025] Example 1 N -Aliphatic substituted amide derivatives 3aa Preparation

[0026] The synthetic route is as follows:

[0027]

[0028] Styrene 1a (91 μL, 0.8 mmol), amine acetal 2a (81.2 mg, 0.2 mmol), Pd(TFA) 2 (3.3 mg, 0.01 mmol), DPPPen (5.3 mg, 0.012 mmol), NH 2 CH 2 CO 2 Me · HCl (5.0 mg, 0.04 mmol), H 2 O (4 μL, 0.22 mmol) is added to 1.0 mL of anisole, carbon monoxide (10 atm), 120 o After C reacted for 21 hours, the reaction was stopped, n-hexadecane was added as the internal standard, the GC yield was 87%, the solvent was evaporated, and the column chromatography was ethyl acetate / petroleum ether (1:10) to obtain the pure amide derivative 3aa . The product was a white solid with a yield of 72%.

[0029] 1 (400 MHz, CDCl 3 ) δ 2.70 (dd, J 1 = 7.4 Hz, J 2 = 10.4 Hz, 2H), 3.03 (dd, J 1 = 7.4 Hz, J 2 = 10.4 Hz, 2H), 4.37 (s, 2H), 4.60 (s, 2H), 7.06 (d, J = 6.9 Hz, 2H), 7.19-7.21 (m, 5H), 7.24-7.35 (m, 8H);

[0030] 13 C NMR (100 MHz, CDCl 3 ) δ 31.6, 35.1...

Embodiment 2

[0032] Example 2 N -Aliphatic substituted amide derivatives 3aa Preparation

[0033] Styrene 1a (91 μL, 0.8 mmol), amine acetal 2a (81.2 mg, 0.2 mmol), PdCl 2 (0.01 mmol), DPPPen (5.3 mg, 0.012 mmol), NH 2 CH 2 CO 2 Me · HCl (5.0 mg, 0.04 mmol), H 2 O (4 μL, 0.22 mmol) is added to 1.0 mL of anisole, carbon monoxide (10 atm), 120 o After C reacted for 21 hours, the reaction was stopped, n-hexadecane was added as an internal standard, and the GC yield was 63%.

Embodiment 3

[0034] Example 3 N -Aliphatic substituted amide derivatives 3aa Preparation

[0035] Styrene 1a (91 μL, 0.8 mmol), amine acetal 2a (81.2 mg, 0.2 mmol), Pd(OAc) 2 (0.01 mmol), DPPPen (5.3 mg, 0.012 mmol), NH 2 CH 2 CO 2 Me · HCl (5.0 mg, 0.04 mmol), H 2 O (4 μL, 0.22 mmol) is added to 1.0 mL of anisole, carbon monoxide (10 atm), 120 o After C reacted for 21 hours, the reaction was stopped, n-hexadecane was added as an internal standard, and the GC yield was 54%.

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Abstract

The invention discloses a preparation method for fatty acyl amide, belonging to the technical field of organic chemical synthesis. The method comprises the following steps: using substituted terminal olefin, carbon monoxide, and aminal or amine as raw materials, then carrying out catalyzation or co-catalyzation with aldehyde via a transition metal catalyst, and carrying out reaction in an organic solvent at 50 to 120 DEG C for 12 to 24 hours under the participation of a ligand or the co-participation of the ligand with an additive; removing the organic solvent when the reaction is completed, and carrying out column chromatography so as to obtain a fatty acyl amide compound. The preparation method for the fatty acyl amide has the following advantages: the raw materials, the catalyst and the additive for the reaction are cheap and easily available; synthetic process is simple; synthetic cost is greatly reduced; reaction conditions are mild; industrialization is easily realized; the raw materials and the catalyst for the reaction are clean and non-toxic and has small pollution to the environment.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a method for preparing fatty amides. Specifically, substituted terminal olefins, carbon monoxide, and amine acetals or amines are used as raw materials to generate hydrogen through transition metal catalysts or co-catalyzed with aldehydes. Amine carbonylation reaction to obtain compounds with fatty amide structure. Background technique [0002] As an important fine chemical, amides are widely used in pesticides, pharmaceuticals, spices and other industries. The amide group is a common pharmacophore, which widely exists in various natural products and synthetic drugs with physiological activity, and is also a fragment of various functional materials. For example, sulpiride has a better effect on symptoms of apathy, withdrawal, stupor, depression, hallucinations and delusions, and is suitable for schizophrenia simple type, paranoid type, catatonic type and chronic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B43/06C07C231/10C07C233/11C07C235/34C07C233/05C07C233/13C07C233/07C07D295/185C07D213/56
Inventor 黄汉民张国营
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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