13080-74-5

Basic information

• Product Name: 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine
• CAS NO: 13080-74-5
• Molecular Weight: 264.154
• Mol File: 13080-74-5.mol

Chemical Properties

• Melting Point: 114-115 °C
• Boiling Point: 365.9±42.0 °C(Predicted)
• Density: 1.296±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine(13080-74-5)
• EPA Substance Registry System: 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine(13080-74-5)

Safety Data

• Hazardous Substances Data: 13080-74-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine is used as a key intermediate in the synthesis of Dichloroimipramine Hydrochloride (D434845). 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine is an analog of Imipramine Hydrochloride (I465980), which is a well-known tricyclic antidepressant. The development of Dichloroimipramine Hydrochloride aims to improve the efficacy and safety profile of tricyclic antidepressants, potentially offering better treatment options for patients suffering from depression.
In the synthesis process, 3,7-Dichloro-10,11-dihydro-5H-dibenz[b,f]azepine serves as a building block for the formation of the final drug molecule. Its unique chemical structure allows for further functionalization and modification, enabling the creation of new analogs with improved pharmacological properties. The use of this intermediate in the pharmaceutical industry highlights its importance in the development of novel therapeutic agents for the treatment of various mental health disorders.

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Relevant articles and documents

A depression drug impurity of preparing method (by machine translation)

The invention relates to a depression drug impurity of preparing method, it comprises the following steps: (a) the high sodium iodate, water and mixed DMF; (b) is poured into ice water, adjusting pH with alkali and layered extraction, purification to obtain compound 4; in the 120 - 150 °C reaction after column chromatography separation to obtain compound 5; (c) the compound 3 and said compound 5 by adding ethylene glycol dimethyl ether, in the ice water bath under the conditions of the adding sodium hydride to, heating up to 40 - 60 °C reaction 20 - 40 minutes, further heating up to reflux; (d) the compound 6 with the [...] catalyst, morpholine, methanol and ethanol are mixed, the reaction is carried out in a hydrogen atmosphere, filtered [...] filtrate to obtain compound 7; (e) the compound 7 with formic acid, a sodium mixed, heated to 100 - 120 °C refluxing reaction; (g) the compound 10 in toluene soluble, in an inert gas atmosphere by adding sodium hydride, temperature reaction. This can obtain the high purity of the depression drug impurity isomer, for impurity accurate control. (by machine translation)

Preparation method of impurity isomer key intermediate of anti-depressive drug

The invention relates to a preparation method of an impurity isomer key intermediate of an anti-depressive drug. The preparation method comprises the following steps: (a) mixing sodium periodate, water and DMF (Dimethylformamide); (b) pouring in ice water, adjusting pH with an alkaline solution, extracting by layers, purifying to obtain a compound 4, and performing column chromatography isolationafter reacting at 120 to 150 DEG C to obtain a compound 5; (c) adding the compound 3 and the compound 5 into 1,2-dimethoxyethane, adding sodium hydride under the condition of ice water bath, heating to 40 to 60 DEG C for reacting for 20 to 40 minutes, and heating and refluxing; (d) mixing the compound 6 with a rhodium carbon catalyst, morpholine, methanol and ethanol, reacting under a hydrogen atmosphere, and performing suction filtration and spin drying on filtrate to obtain a compound 7; (e) mixing the compound 7 with formic acid and sodium formate, and heating to 100 to 120 DEG C for refluxreaction; (f) adding anhydrous K2CO3,Cu powder and CuBr, performing reaction under the protection of insert gas at the temperature of 150 to 180 DEG C to obtain a compound 9; cooling to 30 to 60 DEGC, adding NaOH solution to perform reaction, filtering, and purfying to obtain a compound 10.. By adopting the preparation method, a high-purity impurity isomer of the anti-depressive drug can be obtained for accurate control of impurities.

Preparation method of chloronitrophenyl intermediate serving as impurity isomer of medicine for treating depression

The invention relates to a preparation method of a chloronitrophenyl intermediate serving as an impurity isomer of medicine for treating depression. The method includes the following steps that a, sodium periodate, water and DMF are mixed, then a DMF solution of a compound 2 is added for a reaction, and after the reaction, a filtrate is taken and purified to obtain a compound 3; b, 2-bromo-4-chlorotoluene, N-bromosuccinimide, dibenzoyl peroxide and carbon tetrachloride are mixed, stirred, heated to 80-100 DEG C for a reaction and then poured into ice water, the pH is adjusted with lye, and layered extraction and purification are conducted to obtain a compound 4; c, the compound 3 and a compound 5 are added into glycol dimethyl ether, sodium hydride is added under the condition of an ice water bath, the temperature is raised to 40-60 DEG C for a reaction for 20-40 minutes, then the temperature is raised for reflux, after the reaction is completed, water and ethyl acetate are added in avolume ratio of 1:1, and solid is precipitated, subjected to suction filtration and dried to obtain a compound 6. In this way, the nitrophenyl intermediate with high purity can be obtained to be usedfor subsequent preparation of the high-purity and high-yield impurity isomer of medicine for treating depression.

Synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines; key synthons in syntheses of pharmaceutically active compounds

Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from commercially available 2-bromotoluenes or 2-nitrotoluenes. Initial α-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester derivatives. After reaction with benzaldehyde derivatives, the expected Horner-Emmons reaction products were obtained. Hydrogenation gave the amino derivatives which were transformed into the corresponding formamides. Under Goldberg conditions [1], the final ring closing step was performed to give the substituted 10,11-dihydro-5H-dibenz[b,f]azepines in 46-75% yield.