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A kind of synthesis technique of 1-benzhydrylazetidine-3-carbaldehyde

A technology of diphenylmethyl azetidine and synthesis process, which is applied in the field of synthesis technology of 1-diphenylmethyl azetidine-3-formaldehyde, and achieves simple operation, convenient post-processing and total yield high effect

Active Publication Date: 2019-03-26
江苏安杰泰生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-Benzhydrylazetidine-3-carbaldehyde is a very versatile linking block in medicinal chemistry, but there are few literature reports on the synthesis of this compound

Method used

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  • A kind of synthesis technique of 1-benzhydrylazetidine-3-carbaldehyde
  • A kind of synthesis technique of 1-benzhydrylazetidine-3-carbaldehyde

Examples

Experimental program
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Embodiment 1

[0023] (1) Synthesis of 1-benzhydrylazetidine-3-bromide

[0024] Dissolve 1-benzhydrylazetidin-3-ol (240.0g, 1.0mol) in dry 1200ml of chloroform, add triethylamine (111.3g, 1.1mol), then cool to 0°C , add phosphorus tribromide (270.7g, 1.0mol) dropwise, the dropwise addition time is 4 hours, the temperature is controlled not to exceed 10°C during the dropwise addition process, after the dropwise addition, react at 0-5°C for 3 hours, then ice Wash with water (200mL × 2), adjust the pH value to 7 with 1% sodium hydroxide solution, then wash with 200 ml of ice water, after standing for layers, concentrate under reduced pressure to obtain a white solid product (256.7g, yield 85%). 1 H NMR (CDCl 3 ,300MHz)δ:7.41-7.43(m,4H),7.28-7.31(m,4H),7.20-7.23(m,2H),4.50-4.52(m,2H),3.79-3.82(m,2H), 3.39-3.42 (m, 2H).

[0025] (2) Synthesis of 1-benzhydrylazetidine-3-carbaldehyde

[0026] Put magnesium chips (24.0g, 1.0mol) in a 1-liter three-necked flask, add 100ml of dry tetrahydrofuran,...

Embodiment 2

[0028] (1) Synthesis of 1-benzhydrylazetidine-3-bromide

[0029] Dissolve 1-benzhydrylazetidin-3-ol (240.0g, 1.0mol) in dry 1000ml of dichloromethane, add potassium carbonate (151.8g, 1.1mol), then cool to 0 ℃, add phosphorus tribromide (311.3g, 1.2mol) dropwise, the dropwise addition time is 4 hours, control the temperature not to exceed 10°C during the dropwise addition process, after the dropwise addition, react at 0-5°C for 3 hours, then Wash with ice water (200mL × 2), adjust the pH value to 7 with 1% sodium hydroxide solution, then wash with 200 ml of ice water, after standing for layers, concentrate under reduced pressure to obtain a white solid product (265.8g, harvested rate 88.0%). 1 H NMR (CDCl 3 ,300MHz)δ:7.41-7.43(m,4H),7.28-7.31(m,4H),7.20-7.23(m,2H),4.50-4.52(m,2H),3.79-3.82(m,2H), 3.39-3.42 (m, 2H).

[0030] (2) Synthesis of 1-benzhydrylazetidine-3-carbaldehyde

[0031] Put magnesium chips (36.0g, 1.5mol) in a 1-liter three-necked flask, add 200ml of dry d...

Embodiment 3

[0033] (1) Synthesis of 1-benzhydrylazetidine-3-bromide

[0034] Dissolve 1-benzhydrylazetidin-3-ol (240.0g, 1.0mol) in dry 1200ml of 1,2-dichloroethane, add pyridine (94.9g, 1.2mol), Then cool to 0°C, add phosphorus tribromide (297.8g, 1.1mol) dropwise, the dropwise addition time is 4 hours, control the temperature not to exceed 10°C during the dropwise addition, and react at 0-5°C after the dropwise addition 3 hours, then washed with ice water (200mL × 2), adjusted the pH value to 7 with 1% sodium hydroxide solution, then washed with 200 ml of ice water, left to stand and concentrated under reduced pressure to obtain a white solid product ( 271.8g, yield 90%). 1 H NMR (CDCl 3 ,300MHz)δ:7.41-7.43(m,4H),7.28-7.31(m,4H),7.20-7.23(m,2H),4.50-4.52(m,2H),3.79-3.82(m,2H), 3.39-3.42 (m, 2H).

[0035] (2) Synthesis of 1-benzhydrylazetidine-3-carbaldehyde

[0036]Put magnesium chips (36.0g, 1.5mol) in a 1-liter three-necked flask, add 250ml of dry methyltetrahydrofuran, and warm ...

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Abstract

The invention discloses a process for synthesizing 1-benzhydrylazetidin-3-formaldehyde. The process includes the following specific steps: (1) under the action of an alkali, subjecting 1-benzhydrylazetidin-3-ol and phosphorous tribromide to reaction in a dried aprotic solvent to obtain 1-benzhydrylazetidin-3-bromo; (2) in a dried solvent, subjecting the 1-benzhydrylazetidin-3-bromine to reaction with magnesium chips to generate form Grignard reagent; subjecting the Grignard reagent to reaction with dried DMF (dimethyl formamide), carrying quenching reaction with ammonium chloride after reaction, and post-treating to obtain the target product 1-benzhydrylazetidin-3-formaldehyde. The process of the invention is stable to perform, high in yield, low in output of three wastes and low in production cost. The produced product has good quality.

Description

technical field [0001] The invention relates to a synthesis process of 1-benzhydrylazetidine-3-carbaldehyde, which belongs to the technical field of organic synthesis. Background technique [0002] Nitrogen-containing heterocyclic compounds usually have unique biological activity, low toxicity and high systemic property, and are often used as structural units of medicines and pesticides. Nitrogen-containing heterocyclic compounds are easy to carry out structural modification, and various functional groups can be introduced conveniently. 1-Benzhydrylazetidine-3-carbaldehyde is a very versatile linking block in medicinal chemistry, but there are few literature reports on the synthesis of this compound. Contents of the invention [0003] Aiming at the deficiencies in the prior art, the object of the present invention is to provide a synthesis process of 1-benzhydrylazetidine-3-carbaldehyde. The synthesis process is stable in operation, high in yield, less in three wastes, l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D205/04
CPCC07D205/04
Inventor 吴岳林马建江陆芳柳
Owner 江苏安杰泰生物科技有限公司