Hydrochloric Acid → 136564-89-1

Temperature

0 °C

To a suspension of lithium aluminum hydride (15.5 g) in diethyl ether (290 ml) was added a solution of 2-methyl-4,4,4-trifluorobutyramide (31.74 g) in diethyl ether (0.5 L) at a rate to obtain a gentle reflux. After heating at reflux for 12 hours and cooling to 0° C., the reaction was quenched with saturated sodium sulfate solution and allowed to warm to ambient temperature. The mixture was dried (Na2SO4) and filtered through diatomaceous earth with diethyl ether wash. The filtrate was treated with gaseous hydrochloric acid (14.9 g, 0.409 mol) and then the solvent was evaporated. The residue was dissolved in methylene chloride and combined with product from a similar reaction of 2-methyl-4,4,4-trifluorobutyramide (25 g). Recrystallization from methylene chloride and diethyl ether, followed by trituration with ethyl acetate, afforded 2-methyl-4,4,4-trifluorobutylamine hydrochloride (51.35 g, 79%) as a light pink solid; mp 224.5°-225.5° C.; MS(CI): 142 (M+H-HCl). Analysis for C5H11ClF3N: Calculated: C, 33.81; H, 6.24; N, 7.89. Found: C, 33.93; H, 6.13; N, 8.17.

1. customto obtain a gentle reflux
2. temperatureAfter heating
3. temperatureat reflux for 12 hours
4. customthe reaction was quenched with saturated sodium sulfate solution
5. temperatureto warm to ambient temperature
6. dry with materialThe mixture was dried (Na2SO4)
7. filtrationfiltered through diatomaceous earth with diethyl ether
8. washwash
9. customthe solvent was evaporated
10. dissolutionThe residue was dissolved in methylene chloride
11. customcombined with product from a similar reaction of 2-methyl-4,4,4-trifluorobutyramide (25 g)
12. customRecrystallization from methylene chloride and diethyl ether

ORD record

ord-35a9c5ed1c6046029fceeaa480e06c44

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05286740