Bromoacetonitrile → 2-(4-hydroxypiperidin-1-yl)acetonitrile

HRID 226242Notes

Reaction equation

Br[CH2:2][C:3]#[N:4].[OH:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1>C1COCC1.CCN(CC)CC>[OH:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:2][C:3]#[N:4])[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 47.5 °C

Procedure

BrCH2CN (28.55 g, 0.238 mmol) was added dropwise to a solution of 4-hydroxypiperidine (24.98 g, 0.216 mol) and Et3N (33.18 mL, 0.238 mmol) in dry THF (100 mL) under N2, maintaining the temperature between 45-50° C. After addition of BrCH2CN, the solution was refluxed for 30 min., before allowing the solution to cool down to room temperature. The title-compound was afforded as a straw-coloured oil (18.97 g, 63%) after purification by flash chromatography using ether/CH3OH (19:1) as eluent. dH (250 MHz; CDCl3); 1.65 (m, 2H, 1×CH2CH2CH and 1×CHCH2CH2), 1.75 (s, 1H, OH), 1.95 (m, 2H, 1×CH2CH2CH, 1×CHCH2CH2), 2.45 (m, 2H, 1×NCH2CH2 and 1×NCH2CH2), 2.78 (m, 2H, 1×NCH2CH2 and 1×NCH2CH2), 3.55 (s, 2H, NCH2CN) and 3.75 (m, 1H, CH2CHOH); δC (62.9 MHz; CDCl3); 33.96, 46.09, 49.73, 66.58 and 114.71 (CN); IR υmax/cm−1; 3375(broad), 2230, 1420, 1330, 1150 and 1060; FAB MS, m/z(M+H)+ 141.

Workup

temperaturethe solution was refluxed for 30 min.
temperatureto cool down to room temperature

Sources & evidence

ORD record: ord-81f333496a744007920a800d6c02df9c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557215B2

Reaction notes

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