Acetic Anhydride → N-(1-(Cyclohexylmethyl)piperidin-4-yl)-N-((4-methylphenyl)methyl)-4-methoxyphenylacetamide

The product from example 13 above (20 mg, 0.06 mmol) was dissolved in abs. ethanol (2 ml). Cyclohexanecarboxaldehyde (0.138 ml, 1.1 mmol) was added followed by solid-supported borohydride (150 mg, 2.5 mmol/g resin; Aldrich 32,864-2). The mixture was shaken at room temperature. After 48 h, the resin was filtered off and acetic anhydride (0.02 ml, 0.2 mmol) was added to the organic solution. After 24 h, the mixture was concentrated and redissolved in methanol (2 ml). The solution was added on to a column carrying strongly acidic cation exchange resin (0.3 mmol/g resin), which was washed with methanol (3×6 ml), and eluted with 10% NH3 in methanol, and concentrated to give the title compound. Yield: 17 mg; HRMS (FAB+, NBA) (M+H)+ 449.3163, C29H41N2O2 requires 449.3168; LC-MS: (M+H)+ 449.2, tr 7.92 min.

1. filtrationthe resin was filtered off
2. waitAfter 24 h
3. concentrationthe mixture was concentrated
4. dissolutionredissolved in methanol (2 ml)
5. additionThe solution was added on to a column
6. washwas washed with methanol (3×6 ml)
7. washeluted with 10% NH3 in methanol
8. concentrationconcentrated

ORD-Eintrag

ord-5a2bbbc9c6224847b5593745e94f5d60

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06756393B2