N,N,N',N'-Tetramethyl-1,3-diaminopropane → Methyl 4-((1-(4-bromo-2-methylphenyl)-2-methylpropyl)amino)benzoate

Temperature

60 °C

To a mixture of 1-(4-bromo-2-methylphenyl)-2-methylpropan-1-ol (600 mg), N,N,N′,N′-tetramethyl-1,3-propanediamine (0.492 mL) and toluene (0.823 mL) was added methanesulfonyl chloride (0.229 mL), and the mixture was stirred at 60° C. for 2 hr. To the reaction mixture were added methyl 4-aminobenzoate (560 mg) and N,N-diisopropylethylamine (0.862 mL) at room temperature, and the mixture was stirred at 100° C. overnight under a nitrogen atmosphere. To the reaction mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (457.4 mg).

1. stirringthe mixture was stirred at 100° C. overnight under a nitrogen atmosphere
2. extractionthe mixture was extracted with ethyl acetate
3. washThe extract was washed with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-18bfe7efb3b74d868b7305481b16d707

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073864B2