Triethylamine → 1-[(4-Methoxyphenyl)methyl]-4-piperidinol

To a stirred solution of 4-hydroxypiperidine (0.97 g, 9.60 mmol) in anhydrous dimethylformamide (20 mL) at 0° C. was added 1-(bromomethyl)-4-methoxybenzene (1.93 g, 9.60 mmol) and triethylamine (2.16 g, 21.4 mmol). The reaction mixture was then warmed to room temperature and stirred overnight. After this time the mixture was concentrated under reduced pressure and the resulting residue was dissolved in ethyl acetate (40 mL), washed with water (20 mL), then brine (20 mL) and dried over sodium sulfate. The drying agent was filtered off and the filtrate concentrated under reduced pressure. The residue obtained was purified by flash chromatography (silica gel, 0-5% methanol/methylene chloride) to afford 1-(4-methoxybenzyl)piperidin-4-ol as a brown oil (1.70 g, 80%). 1H-NMR (CDCl3, 300 MHz): δ 7.27 (d, J=7.8 Hz, 2H), 6.86 (d, J=7.8 Hz, 2H), 3.79 (s, 3H), 3.76 (m, 1H), 3.55 (s, 2H), 2.81 (m, 2H), 2.29 (m, 2H), 1.96 (m, 2H), 1.64 (m, 3H); MS (ESI): 222.1 (M+H).

1. concentrationAfter this time the mixture was concentrated under reduced pressure
2. dissolutionthe resulting residue was dissolved in ethyl acetate (40 mL)
3. washwashed with water (20 mL)
4. dry with materialbrine (20 mL) and dried over sodium sulfate
5. filtrationThe drying agent was filtered off
6. concentrationthe filtrate concentrated under reduced pressure
7. customThe residue obtained
8. customwas purified by flash chromatography (silica gel, 0-5% methanol/methylene chloride)

ORD record

ord-e5aeb33285fc43c9ba0c824717afaf21

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697727B2