Butylamine → HCID 67745852, compound

Temperature

-18 °C

79.0 g of 5-norbornene-2-carboxaldehyde (NBCXA), (77.6 ml, 0.647 mole) were dissolved in 500 ml of hexane. 47.3 g of n-butylamine (64 ml, 0.647 mole) was slowly added at 25° C. The solution was stirred for five minutes and cooled to -18° C. for several hours. The liquid hexane layer was decanted under nitrogen to remove the precipitated water which had frozen to ice and adhered to the sides of the reaction vessel. The clean hexane solution was removed under nitrogen to a separate reactor and dried with 50 gms of dried 4A molecular sieve. After thirty minutes, the hexane layer containing the n-butyl imine of NBCXA was separated from the molecular sieves and to it was added at -10° C. 80.3 gm (0.647 mole) of diisobutylaluminum hydride as a 15% solution in hexane under nitrogen. The solution was stirred under nitrogen for one hour to yield the MNCM of 5-norbornene-2-methyl-(N-n-butyl) amine. The reactions are summarized below: ##STR40##

1. customThe liquid hexane layer was decanted under nitrogen
2. customto remove the precipitated water which
3. temperaturehad frozen to ice
4. customThe clean hexane solution was removed under nitrogen to a separate reactor
5. customdried with 50 gms
6. dry with materialof dried 4A molecular sieve
7. waitAfter thirty minutes
8. additionthe hexane layer containing the n-butyl imine of NBCXA
9. customwas separated from the molecular sieves and to it
10. additionwas added at -10° C
11. stirringThe solution was stirred under nitrogen for one hour

ORD record

ord-4b01b6bed07845af81cce6d049e3d62c

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05376153