Acetic Acid → N,N-Diethyl-1-heptanamine

Dissolve 50.90 ml (0.5 moles) diethylamine and 57.10 g (0.5 mole) heptaldehyde in 500 ml methanol and stir at room temperature for one hour. Slowly add 31.42 g sodium cyanoborohydride in 500 ml methanol to the stirred reaction mixture. Add glacial acetic acid to the reaction mixture until pH=6. Stir at room temperature overnight. Concentrate reaction mixture volume to 300 ml and then add 500 ml distilled water. Add concentrated hydrochloric acid until pH=1. Extract with 5×250 ml methylene chloride. Evaporate organic solvent and then dissolve the residue in 400 ml 0.1N HCl. Wash aqueous solution with 3×200 ml diethyl ether and then add 2N NaOH until solution is basic (pH=12). Extract with 3×200 ml diethyl ether. Dry over MgSO4, filter and evaporate, the distill in vacuo to obtain 46.0 g (53.7%) title compound.

1. stirringStir at room temperature overnight
2. concentrationConcentrate
3. customreaction mixture volume to 300 ml
4. additionadd 500 ml
5. distillationdistilled water
6. additionAdd concentrated hydrochloric acid until pH=1
7. extractionExtract with 5×250 ml methylene chloride
8. dissolutionEvaporate organic solvent and then dissolve the residue in 400 ml 0.1N HCl
9. additionWash aqueous solution with 3×200 ml diethyl ether and then add 2N NaOH until solution
10. extractionExtract with 3×200 ml diethyl ether
11. dry with materialDry over MgSO4
12. filtrationfilter
13. customevaporate
14. distillationthe distill in vacuo

ORD record

ord-965b79877d214b8baeae430086632459

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04545995