4-(1-Methylpiperidin-4-yloxy)-3-trifluoromethylbenzonitrile → HCID 67500259, compound

HRID 1919827Notes

Reaction equation

HRID 1919827 reaction equation
F[C:2](F)(F)[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1.CN1CC[CH:20](OC2C=CC(C#N)=CC=2C(F)(F)F)[CH2:19][CH2:18]1>>[CH:3]1([O:4][C:5]2[N:10]=[CH:9][C:8]([CH:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=2)[CH2:20][CH2:19][CH2:18][CH2:2]1

Participants

3

Reactant 2

HCID 231459404-(1-Methylpiperidin-4-yloxy)-3-trifluoromethylbenzonitrileHCID 58629100HCID 58629100, compound

Product 1

HCID 67500259HCID 67500259, compound

Procedure

The title compound was synthesized according to the procedure described for the synthesis of 1-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]ethanamine, step B, starting from 4-[(1-methylpiperidin-4-yl)oxy]-3-(trifluoromethyl)benzonitrile. Yield 49 mg, 62% (oil) after column chromatography on silica gel (eluent: CHCl3/MeOH/conc.NH3, 80:20:1). MS (APCI) m/z 303 [M+H]. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.23 (d, J=6.5 Hz, 3 H), 1.64-1.72 (m, 2 H), 1.86-1.92 (m, 2 H), 2.17 (s, 3 H), 2.21-2.27 (m, 2 H), 2.47-2.55 (m, partly overlapped with DMSO peaks, 2 H), 3.97-4.02 (m, 1 H), 4.55-4.60 (m, 1 H), 7.21 (d, J=8.9 Hz, 1 H), 7.55 (dd, J=8.7, 1.9 Hz, 1 H), 7.60 (d, J=2.0 Hz, 1 H).

Sources & evidence

ORD record
ord-119f38af6e2141f8989157cc78bc5d84
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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