1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene

Uses

1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene may be used for the synthesis of:

• oligomeric thioureas
• bipyrrole-based[2]catenane
• model receptors for dicarboxylates and monosaccharides

General Description

1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene is a protected amine.

Synthesis

The general procedure for the synthesis of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene from di-tert-butyl dicarbonate and 1,4-benzenedimethanamine was as follows: a solution of di-tert-butyl dicarbonate (19.0 g, 87 mmol) in dichloromethane (50 mL) was slowly added dropwise to a cooled-to-0°C suspension of 1,4-benzenedimethanamine (44.0 g, 323 mmol) in dichloromethane ( 200 mL) suspension, and the dropwise addition time was controlled to be more than 30 minutes. Subsequently, the reaction mixture was gradually warmed up to room temperature over 2 hours. Upon completion of the reaction, the reaction mixture was washed with 1N aqueous sodium hydroxide (300 mL), the organic phase was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless solid product. Finally, the product was purified by fast column chromatography with the eluent of dichloromethane:methanol:880 ammonia (94:6:1, v/v, in that order) to afford the target compound 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene as a colorless solid (9.61 g, 47% yield).

References

[1] Journal of Materials Chemistry, 2008, vol. 18, # 41, p. 4917 - 4927
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 19, p. 4189 - 4206
[3] Journal of Organic Chemistry, 1996, vol. 61, # 25, p. 8811 - 8818
[4] Journal of the American Chemical Society, 2008, vol. 130, # 18, p. 6025 - 6039
[5] Patent: WO2004/108675, 2004, A1. Location in patent: Page 115