Water → HCID 14221141, compound

A solution of 4-amino-4-cyano-1-methylpiperidine (3.60 g) in dry dimethoxyethane was added to mechanically stirred suspension of LiAlH4 (3.0 g) in dry dimethoxyethane under nitrogen atmosphere, at such a rate that the temperature didn't rise over 50° C. At the end of the addition the mixture was heated under reflux for 6 hr. Excess LiAlH4 was destroyed by adding to the cold (0° C.) stirred reaction mixture, under nitrogen, 4M NaOH (10 ml), water (3 ml), saturated NaOH solution (10 ml) and water (5 ml). The organic solvent was separated and the aqueous phase was extracted several times with hot THF. The organic solvent which was separated and the THF extracts were combined, dried (Na2SO4) and the solvents were removed to give the title compound as a viscous oil (3.17 g) which was purified by distillation b.p. 60°-62° C. (0.8 mm).

1. customover 50° C
2. additionAt the end of the addition the mixture
3. temperaturewas heated
4. temperatureunder reflux for 6 hr
5. customExcess LiAlH4 was destroyed
6. additionby adding to the cold (0° C.)
7. customreaction mixture
8. customThe organic solvent was separated
9. extractionthe aqueous phase was extracted several times with hot THF
10. customThe organic solvent which was separated
11. dry with materialdried (Na2SO4)
12. customthe solvents were removed

ORD record

ord-b9aceaea826646e684fe658dfa8be422

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05534520