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)

pka

10.06±0.10(Predicted)

form 

Liquid

color 

Pale yellow

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

150349-36-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HS Code 

2924190090

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

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