2-(AMINOMETHYL)-1-METHYLIMIDAZOLE

General procedure: In a stainless steel autoclave (20 mL), equipped with temperature control and magnetic stirrer, was purged 5 times with hydrogen, a solution of imine (3) (3.0 mmol) in CHStep A 2-Aminomethyl-1-methylimidazole To a suspension of lithium aluminum hydride (114 mg, 3.0 mmol) in dry tetrahydrofuran (15 mL) at room temperature in an inert atmosphere was added solid 1-methylimidazole-2-carboxamide (185 mg, 1.5 mmol) [prepared according to J. Org. Chem., 52, 4379 (1987)] in portions. After stirring the reaction mixture for 0.5 hour, the temperature was raised to 50° C. for 3.5 hours. After cooling this reaction, satd. aq. Na2 SO4 (2 mL) was added to quench reaction and then powdered anhyd. Na2 SO4. Filtration of this mixture to remove salts gave a dry solution of 2-aminomethyl-1-methylimidazole in tetrahydrofuran (~25 mL) which was used as is.General procedure: To a solutionof the corresponding aldehyde (1.2 eq.; unless stated otherwise) in DMF (2 inL per 0.3 mmol of aldehyde; unless stated otherwise) was added the corresponding amine (2.5 eq.; unless stated otherwise) and the resulting solution was stirred at 25 C to form the corresponding inline. Then, the corresponding isocyano(tosyl)methyl)arene reagent (1 eq.; unless stated otherwise) and K2CO3 (1.5 eq.; unless stated otherwise*) were added and the reaction mixture was stirred at 25 C (unless stated otherwise). The reaction was stopped after the time indicated for each particular reaction. The reaction progress was monitored by TLC. (0083) A saturated aqueous solution of NH4CI (10 mL per 1 mmol of aldehyde) was added to the reaction mixture, which was then extracted with EtOAc (2 x 30 mL per 1 mmol of aldehyde). The combined organic extracts were washed with H2O (2 x 25 mL per 1 mmol of aldehyde), dried over MgSCC, filtered, and the solvent was evaporated in vacuo to provide the crude product. The residue obtained after the workup was purified using column chromatography or preparative TLC (unless stated otherwise). (0084) * note: in cases when the amine was used as HC1 salt, 4 eq. of K2CO3 were used

Molecular Weight:111.15
XLogP3:-1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:111.079647300
Monoisotopic Mass:111.079647300
Topological Polar Surface Area:43.8
Heavy Atom Count:8
Complexity:74.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes