2-Methylpiperidine → 4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzonitrile

HRID 1630976Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1>CS(C)=O.CCOCC>[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-fluoro-3-(trifluoromethyl)benzonitrile (50.0 g, 0.26 mol, Combi-Blocks AN-1049) and 2-methylpiperidine (156 mL, 1.32 mol) in DMSO (500 mL) was heated at 100° C. under nitrogen for 12 hours. The reaction mixture was diluted with Et2O and washed with water, a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of NH4Cl. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure to give the title compound as a beige powder. UPLC/MS, M−(ESI): 269.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.19 (d, J=2.0 Hz, 1H), 8.12 (dd, J=8.4, 2.0 Hz, 1H), 7.75 (d, J=8.2 Hz, 1H), 3.13 (m, 1H), 2.88 (m, 1H), 2.56 (m, 1H), 1.77-1.25 (m, 6H), 0.72 (d, J=6.0 Hz, 3H).

Workup

washwashed with water
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-bc9f0ffe739b450aafd49f1d62c39d4d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791142B2

Reaction notes

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