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New process for synthesizing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal

A technology of butyraldehyde dimethyl acetal and dimethylamino, which is applied to the preparation of amino hydroxyl compounds, the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, etc., which can solve the problems of low yield, troublesome post-processing, The price of trichloroisocyanuric acid is not cheap and other issues

Inactive Publication Date: 2011-02-02
WISDOM PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The preparation of 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal has some bibliographical reports, but these methods have obvious defects:
[0009] (5) "Fine Chemical Industry" (2002, 19, 385) describes the use of 4-chloro-1-butanol as raw material through oxidation, acetalization and amine solution to prepare 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal, but due to the use of PCC as an oxidant, the post-treatment is very troublesome, has a huge impact on the environment, and the yield is low
[0010] (6) Seetharama et al. reported a route starting from sodium 4-chloro-1-hydroxy-butanesulfonate (Asian. J. Chem. 2008, 20, 6446). Although this route can successfully synthesize the target product, it is also not suitable for scale-up due to the high price of sodium 4-chloro-1-hydroxy-butanesulfonate Production
Because the nitroxide free radical piperidinol and trichloroisocyanuric acid price used in this method are not cheap, and the intermediate 4-chlorobutyraldehyde dimethyl acetal needs to be used in the next step after further underpressure distillation purification, so the There are still some limitations in the process of industrial production
On the other hand, the purity of 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal prepared by this process is only 85-90%

Method used

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  • New process for synthesizing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal
  • New process for synthesizing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal
  • New process for synthesizing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal

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Embodiment 1

[0023] 3L four-neck bottle, equipped with a mechanical stirrer, add CH to the bottle in sequence 2 Cl 2 (450mL), 4-chloro-1-butanol (100 g, effective content 80%) and TEMPO (360 mg), cooled to 0~5°C in an ice bath. NaClO solution (900mL, available chlorine content 7.5%) with saturated NaHCO 3 The pH of the solution was adjusted to between 6.0 and 8.5. The pH-adjusted NaClO solution was dripped into a 3L reaction flask, and the temperature of the system was controlled at 2 Cl 2 Extract (3×150 mL), combine the organic phases, wash with brine, anhydrous MgSO 4 dry. Suction filtration, MeOH (184mL) was added to the filtrate, and H 2 SO 4 (3 mL), stirred at room temperature until the intermediate tetrachlorobutanal disappeared by GC and TLC tracking. 10% NaHCO 3 Aqueous solution (300mL) was added dropwise for washing, the system CH 2 Cl 2 extraction. Combine the organic phases, wash with brine, anhydrous MgSO 4 dry. The organic solvent was removed under reduced pressur...

Embodiment 2

[0026] 1L four-necked bottle, equipped with magnetic stirring, add CH to the bottle sequentially 2 Cl 2 (150mL), 4-chloro-1-butanol (33 g, effective content 80%) and TEMPO (145 mg), cooled to 0~5°C in an ice bath. NaClO solution (300mL, available chlorine content 7.5%) with saturated NaHCO 3 The pH of the solution was adjusted to between 6.0 and 8.5. The NaClO solution with adjusted pH value was dropped into the above 1L reaction flask, and the temperature of the system was kept 2 Cl 2Extract (2×50 mL), combine the organic phases, wash with brine, anhydrous Na 2 SO 4 dry. Filter with suction and remove the organic solvent under reduced pressure to obtain a residue.

[0027] The above residue was dissolved in MeOH (60 mL), and H 2 SO 4 (1 mL), stirred at room temperature until GC and TLC traced to the disappearance of the intermediate 4-chloro-1-butyraldehyde. Add saturated NaHCO dropwise to the system 3 Until the system is alkaline, the organic solvent is removed ...

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Abstract

The invention discloses a new process for synthesizing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal. Particularly, raw material 4-chloro-1-butanol is subjected to three-step reaction of oxidization, acetalation and ammonolysis, and all midbodies are directly used for next reaction without purification, decompressed distillation or refinement. In the step of oxidization reaction, a used oxidant is a sodium hypochlorite aqueous solution for adjusting a pH value, and used catalyst is 2,2,6,6-tetramethylpiperidine oxide. The process for preparing 4-(N,N-dimethylamino)-butyraldehyde dimethylacetal has the characteristics of simple and convenient operation, cheap used reagent, high purity (larger than 95 percent), adaptation of industrial mass production, and the like.

Description

technical field [0001] The invention relates to the technical field of preparation of 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal. Using this new process, 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal can be prepared conveniently and economically, and the purity can reach more than 95%. Background technique [0002] At present, 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal (formula I) is a key intermediate in the synthesis of many drugs, such as rizatriptan benzoate, zolmitriptan, sumatriptan, Melatonin etc. The development of convenient, economical, suitable for industrial production and high-purity synthesis of 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal is of great significance to reduce the manufacturing cost of these drugs. [0003] [0004] The preparation of 4-(N,N-dimethylamino)-butyraldehyde dimethyl acetal has some bibliographical reports, but these methods have obvious defects: [0005] (1) Ahlberg et al. reported a route from 1,4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/40B01J31/02
Inventor 不公告发明人
Owner WISDOM PHARM CO LTD
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