1,3-Oxazolidine → 4-Octanol, 3-amino-

Temperature

40 °C

Catalytic hydrogenation of the 3-nitro-4-octanol to the 3-amino-4-octanol alkanolamine A sample of 3-amino-4-octanol (3A4O) was synthesized by the reduction of the 3-nitro-4-octanol by a Parr Autoclave unit. The stainless steel, 2 liter autoclave was loaded with Grace 3201 Raney Nickel (RaNi, 90 g wet, 45 g dry, 10 wt %) and methanol (MeOH, 300 g). The autoclave was sealed, assembled, purged with nitrogen then hydrogen, pressurized with hydrogen (600 psig), stirred at 600 RPM, and warmed to 40° C. The nitro-alcohol (491 g) was diluted with absolute ethanol (EtOH, 150 g) and pumped into the autoclave (4 ml/min) After 3.5 h the addition was complete and after 4 h the reaction was judged complete as no hydrogen uptake was observed. The autoclave was cooled, stirring stopped, vented, and purged with nitrogen. The autoclave was disassembled and the contents were vacuum filtered to remove the RaNi catalyst. This resulted in the isolation of a light yellow liquid (92 area %) that was concentrated in vacuo (55° C./full vacuum) before product was taken overhead (57-62° C./full vacuum). This resulted in the isolation of a clear, colorless, semi-solid (344 g, 95.3 area %, 75% overall yield) that contained some oxazolidine (2.2 area %) and some secondary amines (0.5 area %).

1. customThe autoclave was sealed
2. custompurged with nitrogen
3. additionThe nitro-alcohol (491 g) was diluted with absolute ethanol (EtOH, 150 g)
4. additionthe addition
5. waitwas complete and after 4 h
6. temperatureThe autoclave was cooled
7. stirringstirring
8. custompurged with nitrogen
9. filtrationfiltered
10. customto remove the RaNi catalyst
11. customThis resulted in the isolation of a light yellow liquid (92 area %) that
12. concentrationwas concentrated in vacuo (55° C./full vacuum) before product
13. custom(57-62° C./full vacuum)
14. customThis resulted in the isolation of a clear, colorless,
15. customsemi-solid (344 g, 95.3 area %, 75% overall yield) that

ORD record

ord-cacaa9f235274082a94171bd38cdab08

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034929B2