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 days. 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. waitthe mixture was hydrogenated at 3 bar pressure for 20 hours
2. filtrationThe mixture was filtered through a glass fibre
3. filtrationfilter paper
4. washwashed with EtOH (2×3 volumes)
5. concentrationthe mother liquor was carefully concentrated
6. customto leave a cloudy brown oil
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationcarefully concentrated in vacuo
10. customto leave an orange oil

ORD record

ord-ecdcf8ed60ff471087545c94bd7f21d6

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455483B2