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| | tert-Butyl N-(3-aminopropyl)-N-methylcarbamate Basic information |
| Product Name: | tert-Butyl N-(3-aminopropyl)-N-methylcarbamate | | Synonyms: | N-(3-AMINO-PROPYL)-N-METHYLCARBAMIC ACID T-BUTYL ESTER;N-(3-AMINOPROPYL)-N-METHYLCARBAMIC ACID TERT-BUTYL ESTER;N-(4-AMINOPROPYL)-N-METHYL CARBAMIC ACID TERT-BUTYL ESTER;1-N-BOC-1-N-METHYL-1,3-DIAMINOPROPANE;(3-AMINO-PROPYL)-METHYL-CARBAMIC ACID TERT-BUTYL ESTER;BUTTPARK 90\06-20;BOC-N-ME-1,3-DIAMINOPROPANE;N-(3-Aminopropyl)-N-methylcarbamic acid tert-butyl | | CAS: | 150349-36-3 | | MF: | C9H20N2O2 | | MW: | 188.27 | | EINECS: | | | Product Categories: | | | Mol File: | 150349-36-3.mol |  |
| | tert-Butyl N-(3-aminopropyl)-N-methylcarbamate Chemical Properties |
| Boiling point | 254.6±19.0 °C(Predicted) | | density | 0.982±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Liquid | | pka | 10.06±0.10(Predicted) | | color | Pale yellow | | Water Solubility | Slightly soluble in water. | | CAS DataBase Reference | 150349-36-3(CAS DataBase Reference) |
| | tert-Butyl N-(3-aminopropyl)-N-methylcarbamate Usage And Synthesis |
| Uses | It is an important raw material and intermediate used in organic synthesis, agrochemicals and dyestuff. | | Synthesis | GENERAL STEPS: Preparation Example 1 Synthesis of tert-butyl-N-(3-aminopropyl)-N-methylcarbamate (2). N-methyl-1,3-propanediamine (1) (3.26 g, 37.03 mmol) was dissolved in methanol (100 ml), and a 35% hydrochloric acid solution was slowly added at 0 °C, followed by stirring. The reaction solution was stirred at room temperature for 30 min, then cooled to -10 °C and di-tert-butyl dicarbonate (10.51 g, 48.14 mmol) was slowly added. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and alkalized with 10% aqueous sodium hydroxide solution. The alkalized solution was extracted with dichloromethane and the organic phase was dried with anhydrous magnesium sulfate. The dried organic phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent ratio: dichloromethane: methanol: ammonia = 100:9:1, v/v/v) to give tert-butyl N-(3-aminopropyl)-N-methylcarbamate (2). Yield: 3.03 g (43%).1H NMR (400 MHz, CDCl3) δ 3.29 (2H, br, -CH2-NH2), 2.83 (3H, s, -N-CH3), 2.69 (2H, t, J = 6Hz, -N-CH2-CH2-), 1.64 (2H, m, -CH2-CH2-CH2-). 1.46 (9H, s, (CH3)3C-O-CO-), 1.38 (2H, s, -CH2-CH2-NH2). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 1073 - 1079
[2] Patent: US2017/81291, 2017, A1. Location in patent: Paragraph 0023; 0046; 0047; 0048
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1565 - 1570 |
| | tert-Butyl N-(3-aminopropyl)-N-methylcarbamate Preparation Products And Raw materials |
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