Piperidin-4-ol → 2,6-Difluoro-4-(4-hydroxy-piperidin-1-yl)-benzonitrile

HRID 2054896Notes

Reaction equation

[F:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>CO>[F:1][C:2]1[CH:9]=[C:8]([N:16]2[CH2:17][CH2:18][CH:13]([OH:12])[CH2:14][CH2:15]2)[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 1.0 g (6.4 mmol) of 2,4,6-trifluorobenzonitrile in MeOH (35 mL) was added 0.65 g (6.4 mmol) of 4-hydroxypiperidine and 1.2 mL (6.7 mmol) of N,N-diiisopropylethylamine. The mixture was heated to 65° C. for 4 h then cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.325 g (21%) of 2,6-difluoro-4-(4-hydroxy-piperidin-1-yl)-benzonitrile as a white solid.

Workup

temperaturethen cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record: ord-a3aa907a578e4b8fa2a854d667438ce5
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329764B2

Reaction notes

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