Cyclobutylmethylamine hydrochloride Chemical Properties

Melting point:

>212°C (dec.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

Off-White to Pale Beige

Stability:

Hygroscopic

InChI

InChI=1S/C5H11N.ClH/c6-4-5-2-1-3-5;/h5H,1-4,6H2;1H

InChIKey

JVZOVVGVPJVLSL-UHFFFAOYSA-N

SMILES

C(C1CCC1)N.Cl

CAS DataBase Reference

5454-82-0

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2922390090

Cyclobutylmethylamine hydrochloride Usage And Synthesis

Chemical Properties

White solid

Synthesis

General procedure for the synthesis of cyclobutylmethylamine hydrochloride from cyclobutanecarbonitrile: A tetrahydrofuran solution of borane (1 M, 296 mL, 296 mmol) was slowly added to a tetrahydrofuran (60 mL) solution of cyclobutanecarbonitrile (20 g, 247 mmol) under argon protection. The reaction mixture was heated to reflux and kept overnight. Upon completion of the reaction, the mixture was cooled in an ice-water bath and methanol (120 mL) was added slowly and dropwise, controlling the reaction temperature below 20 °C. Subsequently, a methanolic solution of 4M hydrochloric acid (300mL) was added and the temperature continued to be controlled below 20°C. The resulting solution was heated and refluxed for 2.5 hours. At the end of the reaction, the mixture was cooled and concentrated. The residue was diluted with methanol (100 mL) and concentrated again and the process was repeated. Ether was added to the residue, stirred for 30 min and filtered to give the title compound cyclobutylmethylamine hydrochloride (25.9 g, 86% yield) as a white solid. NMR hydrogen spectrum (300 MHz, DMSO-d6) δ ppm: 1.70-1.86 (m, 4H), 1.97-2.04 (m, 2H), 2.46-2.61 (m, 1H), 2.75-2.84 (m, 2H), 8.02 (br s, 3H).

References

[1] Patent: WO2015/25164, 2015, A1. Location in patent: Paragraph 59
[2] Patent: US2015/57298, 2015, A1. Location in patent: Page/Page column 19
[3] Patent: WO2011/97491, 2011, A1. Location in patent: Page/Page column 71-72
[4] Patent: WO2005/75464, 2005, A1. Location in patent: Page/Page column 22
[5] Patent: WO2005/74939, 2005, A1. Location in patent: Page/Page column 59

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