Preparation and application of 2-methyl-4-methylaminoisopropanol_Industrial additives

Background and overview^[1]

2-Methyl-4-methylaminoisopropanol can be used in organic synthesis reactions.

Preparation^[1]

2-Methyl-4-methylaminoisopropanol is prepared as follows: Dissolve 1-chloro-2-methyl-2-propanol (103μL, 1.00mmol) in 40% methylamine methanol solution (0.5mL) in a microwave chemical synthesis device (CEMDiscover), stirring at 100W for 15 minutes at 100°C. After cooling to room temperature, the solvent was evaporated under reduced pressure, acetonitrile (3 mL) was added, and the precipitated solid was filtered off. After adding an aqueous sodium bicarbonate solution (10 drops) to the filtrate, the solvent was distilled off under reduced pressure to obtain a crude purified product of 2-methyl-4-methylaminoisopropanol.

Apply^[1]

2-Methyl-4-methylaminoisopropanol can be used to prepare 4-[2-tert-butyl-1-(tetrahydropyran-4-ylmethyl)-1H-imidazol-4-yl] -N-(2-Hydroxy-2-methylpropyl)-N-methylthiophene-2-carboxamide, this compound is a CB2 receptor modulator and is useful as a treatment and/or preventive agent for pain as a treatment for pain such as neuropathic pain, trigeminal neuralgia, diabetic pain, postherpetic neuralgia, neuropathic low back pain, HIV-related pain, fibromyalgia, cancer pain, inflammatory pain, etc. and/or preventive agents are useful. Dissolve [4-(2-tert-butyl-1-cyclohexylmethyl-1H-imidazol-4-yl)phenyl]-piperazin-1-ylmethanone (0.3mmol) in DMF (1.0mL) , add 2-methyl-1-(methylamino)propan-2-ol (0.45mmol), WSC·HCl (86mg, 0.45mmol) and HOBt·H2O (69mg, 0.45mmol), and stir at 60°C 2 hours. After cooling to room temperature, water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50→10/90) to obtain the title compound 4-[2-tert-butyl-1-(tetrahydropyran-4-yl Methyl)-1H-imidazol-4-yl]-N-(2-hydroxy-2-methylpropyl)-N-methylthiophene-2-carboxamide (60 mg, 0.14 mmol, yield 69%) .

Main reference materials

[1] A preparation method of 2-methyl-4-methylaminoisopropanol