Electric Literature of 5805-57-2, The chemical industry reduces the impact on the environment during synthesis 5805-57-2, name is (1H-Benzo[d]imidazol-2-yl)methanamine, I believe this compound will play a more active role in future production and life.
A mixture of 241 (97 mg, 0.25 mmol), (1H-benzimidazol-2-yl)methanamine3 (108 mg, 0.737 mmol), NaBH(OAc)3 (58 mg, 0.27 mmol), and MS4A (80 mg) in CH2Cl2 (8.2 mL) was stirred at room temperature for 10 h. After addition of MeOH, the reaction mixture was partitioned between AcOEt and sat. aq. NaHCO3. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by NH silica gel column chromatography (hexane/CH2Cl2, 1:1-0:1) to give the corresponding amine as pale red oil. To a solution of the amine in EtOH (1.0 mL) was added aq. HCl (2 M, 2.0 mL) and the mixture was heated under reflux for 4 h. The solvent was evaporated, and the residue was partitioned between CH2Cl2 and aq. HCl (1 M). The aqueous layer was basified with aq. NaOH and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (CHCl3/MeOH, 99:1) to give 13 as a free amine. The amine was dissolved in methanolic HCl (2 M) and the solvent was evaporated. The residue was triturated with Et2O to give 13?3HCl (45 mg, 0.12 mmol, 47% for 2 steps) as a pale-brown amorphous solid. 1H NMR (500 MHz, CD3OD) delta 8.76 (1 H, s, imidazole-2), 7.89 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.65 (2 H, dd, J = 6.3, 2.9 Hz, aromatic), 7.32 (1 H, s, imidazole-5), 4.89 (2 H, s, -NCH2Ar), 3.49 (2 H, brs, -CH2CH2N-), 2.04-1.85 (3 H, m, H-1, -CH2CH2N-), 1.34 (1 H, brs, H-2), 1.13 (1 H, brs, H-3a), 1.08 (1 H, brs, H-3b); 13C NMR (125 MHz, CD3OD) delta 144.36, 136.72, 134.40, 133.25, 128.17, 115.99, 115.68, 49.85, 42.96, 30.98, 19.43, 14.37, 13.33; HRMS (EI) calcd for C16H20N5 282.1713, found 282.1715 [(M + H)+]; Anal. Calcd for C16H19N5?3HCl?1H2O: C, 47.02; H, 5.92; N, 17.13. Found: C, 47.15; H, 5.91; N, 17.05.
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Reference:
Article; Watanabe, Mizuki; Kobayashi, Takaaki; Ito, Yoshihiko; Fukuda, Hayato; Yamada, Shizuo; Arisawa, Mitsuhiro; Shuto, Satoshi; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3630 – 3633;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem