Butyric Acid → 4697-92-1

Participants

Reaction Steps

Butyric acid (1.8 g, 19.4 mmol), 1,3-diaminopropane (0.60 g, 8.1 mmol), 1-hydroxybenzotriazole monohydrate (HOBt) (2.4 g, 17.8 mmol) was dissolved in anhydrous DMF (30 mL). 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (3.4 g, 17.8 mmol) was added in small portions at 0° C. and the resulting solution left stirring at room temperature for 15 h. After evaporation of DMF, the solution was taken up with CHCl3 (200 mL) and was washed successively with a 1 M aqueous NaHCO3 solution (30 mL), a 0.1 M aqueous HCl solution (30 mL) abd brine (30 mL). Then the organic layer was dried with anhydrous Na2SO4 and the solvent was removed by rotary evaporation. The resulting residue was precipitated using ether and used in next reaction without further purification. To the precipitate dissolved in THF (50 mL), LiAlH4 (0.40 g, 10.6 mmol) was added slowly at 0° C. The mixture was refluxed overnight, quenched carefully with 0.4 mL of water, 0.4 mL of 15% NaOH and 1.2 mL of water. After filtration on celite, the filtrate was evaporated, dissolved in DCM (100 mL) and extracted with 1N NaOH solution (50 mL). The organic layer dried with anhydrous Na2SO4. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2) providing N,N′-dibutyl-1,3-propanediamine as an oil (0.90 g, 52% (two steps)). 1H NMR (300 MHz, CDCl3): δ 2.67 (t, J=7.0 Hz, 4H), 2.59 (t, J=7.0 Hz, 4H), 1.69 (quin, J=7.0 Hz, 2H), 1.52-1.39 (m, 4H), 1.39-1.24 (m, 4H), 0.91 (t, J=7.2 Hz, 6H); 13C NMR (75 MHz, CDCl3): δ 50.1, 48.9, 32.5, 30.7, 20.7, 14.2; HRMS (ESI): calcd. for C11H26N2[M+H]+ 187.2169. found 187.2170.

Provenance & Evidence