Reaction #452468

Reaction equation

4-bromobenzylbromide

sodium hydride

N-(quinolin-2-yl)propane-1,3-diamine

→

N-(4-bromobenzyl)-N-(quinolin-2-yl)propane-1,3-diamine

Yield 97.3%

Solvents

dimethylsulfoxide

dimethylsulfoxide

dimethylsulfoxide

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 4 days at room temperature
2. 2
   Extractionextracted with ethyl acetate (5×150 ml)
3. 3
   WashThe combined organic extracts were washed with water (4×150 ml)
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent evaporated in vacuo
7. 7
   WashThe residue (22.27 g) was washed with n-heptane (30 ml) which

Procedure

To a mixture of sodium hydride (2.64 g, 60% dispersion in mineral oil, 63.79 mmol) in dry dimethylsulfoxide (100 ml) was slowly added a solution of N-(quinolin-2-yl)propane-1,3-diamine (12 g, 56.62 mmol) in dry dimethylsulfoxide (25 ml) at room temperature under an atmosphere of nitrogen. The reaction mixture was stirred until gas evolution was ceased. To the resulting mixture a solution of 4-bromobenzylbromide (16.27 g, 63.79 mmol) in dry dimethylsulfoxide (50 ml) was slowly added at room temperature. The reaction mixture was stirred for 4 days at room temperature poured on to ice water (800 ml) and extracted with ethyl acetate (5×150 ml). The combined organic extracts were washed with water (4×150 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue (22.27 g) was washed with n-heptane (30 ml) which afforded 20.41 g of crude N-(4-bromobenzyl)-N-(quinolin-2-yl)propane-1,3-diamine which was purified by column chromatography on silica gel (900 ml) using a mixture of dichloromethane/methanol/triethylamine 9:0.5:0.5 as eluent affording 13.9 g (63%) of N-(4-bromobenzyl)-N-(quinolin-2-yl)propane-1,3-diamine as an oil.

Source