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Preparation method of (2-methylamine-ethyl)-tert-butyl carbamate

A technology of carbamic acid and t-butyl carbamate, which is applied in the field of preparation of tert-butyl carbamate, can solve the problems of difficult operation, complex molecular structure, high cost, etc., and achieve the reduction of by-product content, fewer operation steps, and lower The effect of consumption

Active Publication Date: 2019-06-14
上海卡洛化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] According to the analysis, the raw materials used in the first and second synthesis are not sold on the market, and they need to be synthesized by themselves. There are two steps in the synthesis process, and the last step requires the use of precious metals as catalysts for hydrogenation to remove protecting groups, which is difficult to operate. Large, high cost, not suitable for industrial production; and the third to fifth are all using N-methylethylenediamine as raw material, but the yield of the fourth and fifth is too low, not suitable for mass production , and there are by-products produced, which affect the quality of the product; in addition, the third preparation method has a higher yield, but the molecular structure of another raw material is complex, and the cost required for its purchase is relatively large, and the cost is relatively large, so Need to propose a new synthetic route and scheme to synthesize (2-methylamine-ethyl)-tert-butyl carbamate

Method used

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  • Preparation method of (2-methylamine-ethyl)-tert-butyl carbamate
  • Preparation method of (2-methylamine-ethyl)-tert-butyl carbamate
  • Preparation method of (2-methylamine-ethyl)-tert-butyl carbamate

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Embodiment 1

[0043] Embodiment 1: a kind of preparation method of (2-methylamine-ethyl)-tert-butyl carbamate comprises the following steps:

[0044] Step 1. Dissolve 75g of imidazole in 370ml of dichloromethane, and add 228.7g of di-tert-butyl dicarbonate at room temperature. After reacting at room temperature for 2 hours, wash with water three times, each dosage is 150ml; then use anhydrous Sodium sulfate is dried; Subsequent Buchner funnel filtration removes anhydrous sodium sulfate, and at 30 ℃, under the condition of vacuum tightness of 0.08MPa, adopting the mode of underpressure distillation to obtain the intermediate (solid) of 140g after removing methylene chloride ), the reaction equation is as follows:

[0045]

[0046]Step 2. Dissolve 51.6g of the intermediate in 90ml of toluene, then add 27.2g of N-methylethylenediamine, heat to 60°C, react for 2.5 hours, then distill off the toluene under reduced pressure; then add the 100ml dichloromethane as the organic phase, then add 10...

Embodiment 2

[0048] Embodiment 2: a kind of preparation method of (2-methylamine-ethyl)-tert-butyl carbamate, the difference with embodiment 1 is: the consumption of raw material, the temperature of reaction, vacuum degree and reaction time are different , its operation steps are as follows:

[0049] Step 1. Dissolve 75g of imidazole in 352.5ml of dichloromethane, and add 210g of di-tert-butyl dicarbonate at room temperature. After reacting at room temperature for 2 hours, wash with water three times, each dosage is 150ml, and then use anhydrous Sodium sulfate is dried, removes anhydrous sodium sulfate with Buchner funnel filtration subsequently, and at 35 ℃, under the condition of vacuum degree of 0.08MPa, adopt the mode of underpressure distillation to obtain the intermediate of 135g after removing dichloromethane ( solid).

[0050] Step 2. Dissolve 51.6g of the intermediate in 87.72ml of toluene, then add 25.8g of N-methylethylenediamine, heat to 70°C, react for 2 hours, then distill o...

Embodiment 3

[0051] Embodiment 3: a kind of preparation method of (2-methylamine-ethyl)-tert-butyl carbamate, the difference with embodiment 1 is: the consumption of raw material, the temperature of reaction, vacuum degree and reaction time are different , its operation steps are as follows:

[0052] Step 1. Dissolve 75g of imidazole in 390ml of dichloromethane, and add 240g of di-tert-butyl dicarbonate at room temperature, react at room temperature for 3 hours, wash with water three times, each dosage is 200ml, and then use anhydrous sulfuric acid Sodium is dried, then Buchner funnel filtration removes anhydrous sodium sulfate, and at 45 ℃, under the condition of vacuum degree of 0.1MPa, adopt the mode of underpressure distillation to obtain the intermediate (solid) of 142g after removing dichloromethane .

[0053] Step 2. Dissolve 51.6g of the intermediate in 103.2ml of toluene, then add 28.38g of N-methylethylenediamine, heat to 60°C, react for 4 hours, then distill off the toluene und...

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Abstract

The invention discloses a preparation method of (2-methylamine-ethyl)-tert-butyl carbamate, and belongs to the technical field of organic chemical synthesis. The preparation method comprises followingsteps: 1, imidazole is dissolved in dichloromethane, and di-tert-butyl dicarbonate ester is added at room temperature, reaction is carried out for 2 to 3h at room temperature, and water washing drying are carried out so as to obtain an intermediate; and 2, the intermediate is dissolved in toluene, N-methylethylenediamine is added, an obtained mixture is heated to 60 to 70 DEG C, reaction is carried out for 2 to 4h, reduced pressure distillation is carried out to remove toluene, and purification is carried out so as to obtain (2-methylamine-ethyl)-tert-butyl carbamate. The operation steps arefew; by-product content is reduced with ensured (2-methylamine-ethyl)-tert-butyl carbamate synthesis yield; cost is relatively low; and batch production requirements are satisfied.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, more specifically, it relates to a preparation method of (2-methylamine-ethyl)-tert-butyl carbamate. Background technique [0002] (2-Methylamine-ethyl)-tert-butyl carbamate, also known as N-Boc-N'-methylethylenediamine or as 2-(methylamino)ethyl tert-butyl carbamate, the English name is tert-Butyl 2-(methylamino)ethylcarbamate, its CAS number is: 122734-32-1, and its molecular formula is C 8 h 18 N 2 o 2 , whose chemical structure is Its molar mass is 174 g / mol. [0003] There are many ways of synthesizing (2-methylamine-ethyl)-tert-butyl carbamate that are common in the market at present, and the common ones are as follows: [0004] 1. References: WO2013 / 67597A1,; Page / Page column 100 shows, [0005] [0006] 2. References: US2011 / 262355A1,; Page / Page column 136 shows that, [0007] [0008] 3. References: Farmaco,, vol.59, #12p.987-992 shows that the synthetic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/20C07D233/56
Inventor 谭君成
Owner 上海卡洛化学有限公司
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