A common heterocyclic compound, 108468-00-4, name is 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene, molecular formula is C13H20N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 108468-00-4.
Compound 3 (19.6 g, 83.1 mmol, 1 equiv; corresponding to 42.5 g of a mixture with di-Boc-protected 1,4-bis(aminomethyl)benzene, cf. preparation of 3) was suspended in water (500 mL) and ethanol (400 mL). The suspension was heated to 60 C and 1 M aq hydrochloric acid (100 mL) was added yielding a pH of about 3. Potassium cyanate (7 g, 86.3 mmol) was added and the mixture was refluxed for 75 min. 1 M aq hydrochloric acid (8 mL) was added to adjust the pH to 7, followed by the addition of 4.67 g potassium cyanate (4.67 g, 57.6 mmol). Reflux was continued for 2 h, then the mixture was stirred at rt overnight (final pH: ?8) and concentrated under reduced pressure to a volume of about 200 mL. The white solid was separated by filtration, washed twice with water (2 ¡Á 150 mL) and dried in vacuo. A suspension was prepared in a mixture of MeOH and DCM (1:10, 2000 mL) and subjected to column chromatography (DCM/MeOH 20:1-7.5:1). The isolated Boc-protected intermediate (well soluble in MeOH, poorly soluble in water, acetonitrile, ethyl acetate and DCM) was dissolved in MeOH (300 mL) under mild heating. Acetyl chloride (30 mL) was added dropwise over a period of 2 h and stirring was continued for 30 min. Volatiles were removed under reduced pressure and the residue was suspended in water (150 mL). Lyophilisation afforded the product as a white solid (15.8 g, 88%). 1H NMR (300 MHz, MeOH-d4/D2O 80:20): delta (ppm) 4.06 (s, 2H), 4.26 (s, 2H), 7.34 (m, 4H); MS (CI, NH3): m/z 197 [M+NH4]+, 180 [M+H]+; C14H21N3O3 ¡Á HCl (215.8).
The synthetic route of 1-(N-Boc-aminomethyl)-4-(aminomethyl)benzene has been constantly updated, and we look forward to future research findings.
Reference:
Article; Keller, Max; Erdmann, Daniela; Pop, Nathalie; Pluym, Nikola; Teng, Shangjun; Bernhardt, Guenther; Buschauer, Armin; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2859 – 2878;,
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