Bromoacetonitrile → 2-(3-Hydroxypiperidin-1-YL)acetonitrile

Temperature

47.5 °C

BrCH2CN (3.19 g, 25.82 mmol) was added dropwise to a solution of 3-hydroxypiperidine (6.53 g, 64.55 mmol) in dry THF (25 mL) under N2, maintaining the temperature between 45-50° C. Following addition of BrCH2CN, the solution was refluxed for 30 min., before allowing the solution to cool down to room temperature. The solvent was removed in vacuo and the residual oil was purified by flash chromatography using CH2Cl2:CH3OH (9:1) as eluent. The title compound was obtained as a straw-coloured oil (3.04 g, 83%). δh (250 MHz; CDCl3); 1.9-2.15 (m, 3H, CH2CH2CH2, 1×CH2CH2CHOH), 2.25 (m, 1H, 1×CH2CH2CHOH), 2.55 (d, OH), 2.85-3 (m, 3H, NCH2CH2, 1×NCH2CH), 3.1 (2×d, 1H, 1×NCH2CH), 3.9 (s, 2H, NCH2CN) and 4.3 (m, 1H, CH2CHOH); FAB MS, m/z (M+H)+141.

1. temperaturethe solution was refluxed for 30 min.
2. temperatureto cool down to room temperature
3. customThe solvent was removed in vacuo
4. customthe residual oil was purified by flash chromatography

ORD record

ord-7edb0b9f24c44387937a0c66ea93c4a9

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557215B2