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Synthesis method of quetiapine
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A synthesis method and technology of quetiapine are applied in the field of preparation of atypical antipsychotic quetiapine, and can solve the problems of high production cost, low total yield, large pollution and the like
Pending Publication Date: 2022-03-08
GUANGXI TEACHERS EDUCATION UNIV
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[0009] It can be known from the above two routes that the synthetic methods currently used are multi-step synthesis, the steps are more cumbersome, the route is longer, and the operation process is more complicated, the phenomenon of waste of resources is more serious, the pollution is larger, the total yield is lower, and the production cost is relatively high. Relatively high
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Embodiment 1
[0056] Example 1 2-(tert-butyldimethylsilyl)oxy)ethanol
[0057]
[0058] Ethane-1,2-diol (27.5 g, 440 mmol), anhydrous CH 2 Cl 2 (550mL) was added triethylamine (53.53g, 74mL, 530mmol), then the mixture was cooled to 0°C and dissolved in CH 2 Cl 2 (150 mL) of tert-butylchlorodimethylsilane (66.5 g, 440 mol). The mixture was stirred overnight at room temperature. The reaction mixture was washed with saturated NH 4 Aqueous Cl (100 mL) was quenched and separated. The aqueous phase was extracted with methyl tert-butyl ether (2 x 100 mL). The combined organic layers were concentrated under vacuum, and the residue was redissolved in methyl tert-butyl ether (100 mL). The methyl tert-butyl ether layer was washed with water (2x125 mL) and brine (125 mL), dried over anhydroussodiumsulfate, filtered and concentrated in vacuo to give 2-(tert-butyldimethylsilyl)oxy)ethanol ( 69.5 g, 90%).
Embodiment 2
[0059] Example 2 Synthesis of 11-chlorodibenzo[b,f][1,4]thiazoline
[0060]
[0061] Add dibenzo[b,f][1,4]thiazolin-11(10H)-one (9.988g, 44mmol), POCl 3 (7.4g, 4.5ml, 48.4mmol), N,N-dimethylaniline (10.6g, 11ml, 88mmol) and a stirring magnet, the reaction tube was evacuated, filled with argon, added solventtoluene, sealed, and reacted The tube was placed in an oil bath at 110°C for reaction, and the reaction time was 12 hours. After the reaction was completed, the reaction system was cooled to room temperature, 150 ml of water was added, extracted with ethyl acetate (4×300 ml), and the organic phases were combined. After the organic phase was dried over anhydroussodiumsulfate, the solvent was evaporated under reduced pressure. The crude product that obtains uses ethyl acetate: the mixed solvent of sherwood oil (1:10,1:5) as eluent, separates and purifies by column chromatography, purifies and obtains corresponding target product 11-chlorodibenzo[b ,f][1,4]The yield of...
Embodiment 3
[0062] The synthesis of embodiment 3 compound 4
[0063] With 11-chlorodibenzo[b,f][1,4]thiazoline (245mg, 1mmol), 1,4-diazabicyclo[2.2.2]octane (224mg, 2mmol), 2-( tert-Butyldimethylsilyl)oxy)ethanol (176mg, 1mmol) as raw material, Cs 2 CO 3 As base, DMSO as solvent, reacted at 80°C for 12h, and then obtained the target product 4 (198mg, 40%) through silica gelcolumn chromatography.
[0064]
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Abstract
The invention discloses a method for preparing quetiapine, which comprises the following steps: taking 11-chlorodibenzo [b, f] [1, 4] thiazoline, 1, 4-diazabicyclo [2.2. 2] octane and 2-(tert-butyldimethylsilyl) oxy) ethanol as reaction raw materials to obtain an intermediate, and finally hydrolyzing under an acidic condition to obtain quetiapine. The problem that heavy metal exceeds the standard does not need to be considered in the post-treatment process; the generated impurities are relatively reduced, the environmental pollution is less, the method just conforms to the currently advocated green synthesis, and the environment-friendly development of the synthesis production and the environment is embodied.
Description
technical field [0001] The invention belongs to the field of medicines, and in particular relates to a preparation method of quetiapine, an atypical antipsychotic. Background technique [0002] Quetiapine (Quetiapine) is an atypical antipsychoticdrug developed by the British company AstraZeneca and approved by the US FDA in 1997. It has a blocking effect on a variety of neurotransmitter receptors, such as five serotonin receptors (5-HT), dopamine receptors (D), adrenergic receptors (α), cholinergic receptors (M), etc., so It has anti-psychotic, anti-depressant, anti-anxiety, and sedative effects. In 1997, quetiapine was first approved for the treatment of schizophrenia; in 2004, it was approved for the treatment of acute manic episodes; in 2006, it was approved for the treatment of bipolar disorder; Patient compliance is better; in 2009, major depression was added to the indications. Schizophrenia is a severe mental disorder characterized by distortions in thinking, pers...
Claims
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