Butylamine → N-(2,2-dimethoxyethyl)butan-1-amine

To a solution of butan-1-amine (limiting reagent) in EtOH (5 volumes) was added 2,2-dimethoxyacetaldehyde (60%) in water (1 molar equivalent) and the mixture was stirred at room temp for 4 clays. A slurry of 5% palladium on carbon (0.01 molar equivalent) in EtOH (1 volume) was added and the mixture was hydrogenated at 3 bar pressure for 20 hours. The mixture was filtered through a glass fibre filter paper, washed with EtOH (2×3 volumes) and the mother liquor was carefully concentrated to leave a cloudy brown oil. This oil was dissolved in DCM (15 volumes), dried (Na2SO4), filtered and carefully concentrated in vacuo to leave an orange oil. Yield: 101% of theoretical.

1. filtrationThe mixture was filtered through a glass fibre
2. filtrationfilter paper
3. washwashed with EtOH (2×3 volumes)
4. concentrationthe mother liquor was carefully concentrated
5. customto leave a cloudy brown oil
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationcarefully concentrated in vacuo
9. customto leave an orange oil

ORD record

ord-c0d0c288472144f4ab4cb789632f86e8

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476265B2