Butylamine → HCID 67745852, compound

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 diisobutyl aluminum 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: ##STR15##

1. temperaturecooled to -18°°C
2. waitfor several hours
3. customThe liquid hexane layer was decanted under nitrogen
4. customto remove the precipitated water which
5. temperaturehad frozen to ice
6. customThe clean hexane solution was removed under nitrogen to a separate reactor
7. customdried with 50 gms
8. dry with materialof dried 4A molecular sieve
9. waitAfter thirty minutes
10. additionthe hexane layer containing the n-butyl imine of NBCXA
11. customwas separated from the molecular sieves and to it
12. additionwas added at -10°°C
13. stirringThe solution was stirred under nitrogen for one hour

ORD record

ord-763cfda1979042cc9b20e479fd32a3c5

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05271856