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Preparation method of lorcaserin intermediate

A technology for lorcaserin and intermediates, which is applied in the field of preparation of 1-[2--ethylamino]-2-propanol, an intermediate of lorcaserin for weight loss, can solve waste, environmental protection pressure, increase Production costs and other issues, to achieve the effect of simple operation, good safety, and less waste

Pending Publication Date: 2021-02-12
SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In the above route, regardless of the chlorination or bromination reaction, the reagents used, such as thionyl chloride or phosphorus tribromide, are highly corrosive and corrosive to the reaction equipment, and a large amount of acidic tail gas is generated during the reaction. Environmental pressure is high; in the second step of the condensation reaction with isopropanolamine, isopropanolamine is used as both a reactant and an acid-binding agent. Waste, increase production cost, and produce a large amount of nitrogen-containing waste liquid

Method used

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  • Preparation method of lorcaserin intermediate
  • Preparation method of lorcaserin intermediate
  • Preparation method of lorcaserin intermediate

Examples

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Embodiment 1

[0017] Add p-chlorophenylethanol (156.6 g, 1 mol) and 780 ml of 40% hydrobromic acid into the reaction flask, stir and heat up to 80° C., and react for 72 h. The reaction solution was cooled to room temperature, allowed to stand for liquid separation, and the organic phase was washed with water until neutral to obtain 215 g of 4-chlorophenylethyl bromide as a pale yellow oil, with a yield of 98%.

Embodiment 2

[0019] Add 4-chlorophenylethyl bromide (215g, 0.98mol), anhydrous potassium carbonate (149g, 1.08mol), potassium iodide (8.1g, 0.049mol) into the reaction flask, stir and heat up to 60°C, and dropwise add iso Propanolamine (77.3 g, 1.03 mol) was reacted at 60° C. for 4 h after dropping. Cool the reaction solution to room temperature, add 200ml of water to it, stir, and filter to obtain off-white solid 1-[2-(4-chlorophenyl)-ethylamino]-2-propanol, which is air-dried at 50°C to obtain 178g, yield 85%.

Embodiment 3

[0021] Add p-chlorophenylethanol (156.6 g, 1 mol) and 1250 ml of 40% hydrobromic acid into the reaction flask, stir and heat up to 90° C., and react for 48 h. The reaction solution was cooled to room temperature, allowed to stand for liquid separation, and the organic phase was washed with water until neutral to obtain 217 g of 4-chlorophenylethyl bromide as a light yellow oil, with a yield of 99%.

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Abstract

The invention relates to a preparation method of a lorcaserin intermediate 1-[2-(4-chlorphenyl)-ethylamino]-2-propanol, which specifically comprises the following steps: carrying out bromination reaction on p-chlorophenethyl alcohol serving as a starting material to obtain 4-chlorphenyl ethyl bromide, and condensing with isopropanolamine to obtain a target product. Hydrobromic acid is used as a bromination reagent, potassium carbonate is used as a condensation reaction acid-binding agent, potassium iodide is used as a condensation reaction catalyst, the yield of the technological process is high, three wastes are few, the cost is low, the operation is simple, the safety is good, and industrial production requirements are met.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of lorcaserin intermediate 1-[2-(4-chlorophenyl)-ethylamino]-2-propanol. Background technique [0002] Lorcaserin, chemical name (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride hemihydrate, cas: 856681 -05-5, approved by the US FDA in 2012, for obese or overweight adults with a body mass index (BMI) ≥ 27, and the patient has at least one weight-related disease (such as hypertension, type 2 diabetes or Hyperlipidemia). [0003] [0004] 1-[2-(4-chlorophenyl)-ethylamino]-2-propanol (1), cas: 847063-13-2, is an important intermediate required for the synthesis of lorcaserin, reported in the literature Its synthetic route is roughly as follows: [0005] Route 1: p-chlorophenylethanol is chlorinated by thionyl chloride, and then condensed with isopropanolamine. [0006] [0007] Route 2: p-chlorophenylethano...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C215/08C07C17/16C07C25/02
CPCC07C213/08C07C17/16C07C25/02C07C215/08
Inventor 赵思太马新成张宁张宗磊邓玉晓孔祥雨刘文涛冯光玲任业明刘宜辉龚艳艳樊志萍孙晋瑞段崇刚
Owner SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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