Methylamine → 1-Ethyl-N-methyl-4-piperidinamine

To a 40% solution of methylamine in methanol (1.26 g) were added acetonitrile (150 ml), 1-ethyl-4-piperidone (2.0 ml) and acetic acid (0.932 ml), then was added sodium triacetoxyborohydride (6.59 g), followed by stirring for 1 hour. After addition of a saturated aqueous solution of sodium hydrogencarbonate (20 ml), the reaction mixture was concentrated under reduced pressure. To the resultant residue was added methanol (20 ml) to suspend, and the reaction mixture was filtered to remove a solid, which was washed with methanol (20 ml). The filtrate was concentrated under reduced pressure, and tetrahydrofuran (50 ml) was added to the resultant residue to suspend. The reaction mixture was filtered to remove a solid, which was washed with tetrahydrofuran (100 ml). The filtrate was concentrated under reduced pressure to provide a crude product of the titled compound (3.33 g) as pale yellow oil.

1. concentrationthe reaction mixture was concentrated under reduced pressure
2. additionTo the resultant residue was added methanol (20 ml)
3. filtrationthe reaction mixture was filtered
4. customto remove a solid, which
5. washwas washed with methanol (20 ml)
6. concentrationThe filtrate was concentrated under reduced pressure, and tetrahydrofuran (50 ml)
7. additionwas added to the resultant residue
8. filtrationThe reaction mixture was filtered
9. customto remove a solid, which
10. washwas washed with tetrahydrofuran (100 ml)
11. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-e879ab08229041dc944df4d8eb05467f

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531532B2