N-butyl-N-(oxiran-2-ylmethyl)butan-1-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of epichlorohydrin (20.0 g, 0.22 mole) is treated dropwise with di-n-butylamine (29.73 g, 0.23 mole) over a 1 hour period followed by continued stirring at room temperature overnight. The reaction mixture is washed with 20% K2CO3 (50 ml). The organic layer is then stirred with 40% NaOH for 1 hour and then extracted with 3×100 ml portions of ether. The etheral extracts are pooled and washed with H2O (100 ml). The organic layer is dried over anhydrous Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to leave the crude product (I) weighing 39.42 g. The crude product is distilled at 52°/0.15 mmHg to give 8.24 g (20.2%) pure product to be used as an intermediate in Part B. The reaction mixture is washed with 20% K2CO3 (50 ml) The organic layer is then stirred with 40% NaOH for 1 hour extracted with 3×100 ml portions of ether washed with H2O (100 ml) The organic layer is dried over anhydrous Na2SO4 filtered The filtrate is concentrated under reduced pressure to leave the crude product (I) The crude product is distilled at 52°/0.15 mmHg

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of epichlorohydrin (20.0 g, 0.22 mole) is treated dropwise with di-n-butylamine (29.73 g, 0.23 mole) over a 1 hour period followed by continued stirring at room temperature overnight. The reaction mixture is washed with 20% K2CO3 (50 ml). The organic layer is then stirred with 40% NaOH for 1 hour and then extracted with 3×100 ml portions of ether. The etheral extracts are pooled and washed with H2O (100 ml). The organic layer is dried over anhydrous Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to leave the crude product (I) weighing 39.42 g. The crude product is distilled at 52°/0.15 mmHg to give 8.24 g (20.2%) pure product to be used as an intermediate in Part B. The reaction mixture is washed with 20% K2CO3 (50 ml) The organic layer is then stirred with 40% NaOH for 1 hour extracted with 3×100 ml portions of ether washed with H2O (100 ml) The organic layer is dried over anhydrous Na2SO4 filtered The filtrate is concentrated under reduced pressure to leave the crude product (I) The crude product is distilled at 52°/0.15 mmHg