Hexanal → N-hexyl-N',N'-dimethylpropane-1,3-diamine

A solution of n-capronaldehyde (3.79 g, 37.8 mmol) and N,N-dimethylpropane-1,3-diamine (5 mL, 39.7 mmol) in anhydrous methanol (140 mL) was stirred at room temperature for 3 hours. To this solution was added slowly sodium borohydride (2.15 g, 56.8 mmol) over 5 minutes. The solution was stirred for 30 minutes then quenched with 1M NaOH (75 mL), diluted with water (125 mL) and extracted with ethyl acetate (3×150 mL). The combined ethyl acetate extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (gradient: 100% DCM to 10% MeOH in DCM with 1% NH4OH) to afford the title compound as a pale yellow oil (3.79 g, 54%).

1. customthen quenched with 1M NaOH (75 mL)
2. additiondiluted with water (125 mL)
3. extractionextracted with ethyl acetate (3×150 mL)
4. dry with materialThe combined ethyl acetate extracts were dried on magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo to dryness
7. customThe residue was purified by column chromatography (gradient: 100% DCM to 10% MeOH in DCM with 1% NH4OH)

ORD record

ord-cf41c91872bf4504ba1b416d613484c8

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865675B2