N,N,N',N'-Tetramethyl-1,3-diaminopropane → Methyl 4-((1-(4-bromo-2-methylphenyl)-2-methylpropyl)amino)benzoate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH:9]([CH3:11])[CH3:10])=[C:4]([CH3:13])[CH:3]=1.CN(C)CCCN(C)C.CS(Cl)(=O)=O.[NH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1.C(N(CC)C(C)C)(C)C>O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)[CH:9]([CH3:11])[CH3:10])=[C:4]([CH3:13])[CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
Under a nitrogen atmosphere, to a mixture of 1-(4-bromo-2-methylphenyl)-2-methylpropan-1-ol (1.0 g), N,N,N′,N′-tetramethyl-1,3-propanediamine (0.820 mL) and toluene (13.71 mL) was added methanesulfonyl chloride (0.382 mL), and the mixture was stirred at 60° C. for 1.5 hr. To the reaction mixture were added methyl 4-aminobenzoate (0.933 g) and N,N-diisopropylethylamine (1.437 mL) at room temperature, and the mixture was stirred at 100° C. overnight. To the reaction mixture was added water at room temperature, the mixture was extracted with ethyl acetate, and 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 (821.4 mg).
Workup
- stirringthe mixture was stirred at 100° C. overnight
- extractionthe mixture was extracted with ethyl acetate
- washthe extract was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-c536bfee65df464ca0c7ac385dd10009
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073864B2
Reaction notes
Loading…