Acetic Acid → HCID 54793808, compound

To a solution of 4-piperidinemethanol (2.28 g, 19.78 mmol) and 4-methoxybenzaldehyde (2.30 mL, 19.77 mmol) in THF/DCE (1:1 by volume, 100 mL) was added acetic acid (1 mL), followed by NaBH(OAc)3 (16.76 g, 79.08 mmol) in small portions. The reaction mixture was stirred at room temperature overnight under N2. The reaction was diluted with DCM and basified to pH=10 with 2 N NaOH solution. The organic layer was separated, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (Eluent: 60% EtOAc in hexanes) to give the title compound as a pale yellow oil (2.13 g, 46%). 1H NMR (400 MHz, DMSO-d6) δ 1.04-1.13 (m, 2H), 1.28-1.32 (m, 1H), 1.58-1.61 (m, 2H), 1.79-1.86 (m, 2H), 2.75-2.77 (m, 2H), 3.22 (t, J=8.0 Hz, 2H), 3.34 (s, 2H), 3.72 (s, 3H), 4.38 (t, J=4.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H). MS 236 (MH+).

1. customThe organic layer was separated
2. dry with materialdried over Na2SO4
3. filtrationfiltered
4. customevaporated under reduced pressure
5. customThe residue was purified by chromatography on silica gel (Eluent: 60% EtOAc in hexanes)

ORD record

ord-aba16caadddc4febbf392aff64fbb79c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000054B2