2-Propanamine, N-hydroxy-2-methyl-, hydrochloride (1:1)

White to off-white powder

General procedure: A mixture of paraformaldehyde (60 mg, 2 mmol), triethylamine (222 mg, 2.2 mmol) and N-methylhydroxylamine hydrochloride, N-t-butylhydroxylamine or N-benzylhydroxylamine hydrochloride (2 mmol) in anhydrous toluene (10-15 mL) was placed in a glass pressure tube equipped with a magnetic stirrer and stirred at 70 C for 1 h. Only N-cyclohexylhydroxylamine was used as a free base. The solution was cooled to room temperature, the corresponding 1, 3-dimethyluracils 2-5 (1 mmol) was then added, and the solution was heated at 60-80 C for 24-48 h. The solvent was evaporated to dryness under reduced pressure, and 10-15 mL of water was added. The aqueous solution was extracted a few times with CHCl3 and the combined extract dried over Na2SO4. Solvent was removed, and the crude product was separated by column chromatography (silica gel, hexane, a gradient of hexane/CH2Cl2, CH2Cl2 or a gradient of hexane/ethyl acetate) to give compounds 6a-9d. The detailed spectral data ofcompounds 6a-9d and 10a-10d can be found in the Supporting Information, and the representative analytical data of compound 6a are given below.General procedure: A mixture of paraformaldehyde (36 mg, 1.2 mmol), triethylamine (152 mg, 1.5 mmol) and N-methylhydroxylamine hydrochloride or N-t-butylhydroxylamine hydrochloride (1.2 mmol) in anhydrous toluene(10 mL) was placed in a glass pressure tube equipped with a magnetic stirrer and stirred at 40-50C for 1 h. The solution was cooled to room temperature and the corresponding Z- or E-2, 3, 3, 3-tetrafluoroprop-1-enyl derivatives 1a, 1b, 2a or 2b (1 mmol) was then added and the solution was heated at 70 - 80 C for 24-48 h. The reactions were monitored by TLC. Then the solvent was evaporated, the residue was dissolved in 10 mL of water and extracted with CHCl3 (3×10 mL). The organic layers were dried with Na2SO4 and evaporated under reduced pressure to afford a crude mixture which was purified by column chromatography (silica gel, a gradient of hexane/CHCl3 and next agradient of CHCl3/CH3OH, or a gradient of hexane/CH3CO2C2H5).

Molecular Weight:125.60
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:125.0607417
Monoisotopic Mass:125.0607417
Topological Polar Surface Area:32.3
Heavy Atom Count:7
Complexity:37.3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes