Methylamine → N-Methyl-1-(methylsulfonyl)-4-piperidinamine

1-Methylsuylfonyl-4-piperidone (40.00 g, 0.226 mol), CH3CN (240 ml) and 40% CH3NH2 (20.4 ml, 0.263 mol) were added to a round bottom flask, and the mixture was stirred at room temperature for 1 hour. To another round bottom flask, NaBH(OAc)3 (60.00 g, 0.283 mol) and 120 ml of CH3CN were added. This solution was stirred at −10° C., to which the first mixture (derived from 1-methylsulfonyl-4-piperidone) was added slowly via an additional funnel. After the addition, the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentarted to a small volume, to which 1N aq. NaOH (282 ml) was added. This resulting solution was extracted with CH2Cl2 (3×500 ml) followed by extraction with toluene until no product remained in the extraction solution. The combined organic layers were dried over Na2SO4. After filtration, the solution was concentrated in vacuo to give the product (29.0 g, 63%). 1H NMR (CDCl3) δ 3.66 (m, 2H), 2.84 (m, 2H), 2.76 (s, 3H), 2.52 (m, 1H), 2.42 (s, 3H), 1.96 (m, 2H), 1.45 (m, 2H). MS m/e 193 (M+H)+.

1. additionwas added slowly via an additional funnel
2. additionAfter the addition
3. temperatureto warm to room temperature
4. stirringstirred overnight
5. additionwas added
6. extractionThis resulting solution was extracted with CH2Cl2 (3×500 ml)
7. extractionfollowed by extraction with toluene until no product
8. dry with materialThe combined organic layers were dried over Na2SO4
9. filtrationAfter filtration
10. concentrationthe solution was concentrated in vacuo

ORD-Eintrag

ord-c61c8e17c75949049c4a8c6a657f4b12

Quelldatensatz

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07304076B2