Trimethylsilyl iodide → 4-Amino-4-methyl-1-(5-trifluoromethyl-2-pyridyl)piperidine

HRID 855836Notes

Reaction equation

C(OC(=O)[NH:10][C:11]1([CH3:27])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C>[CH3:27][C:11]1([NH2:10])[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4-methyl-5′-trifluoromethyl-3,4,5,6-tetrahydro-2H-(1,2′)bipyridinyl-4-yl)-carbamic acid benzyl ester (0.37 g, 0.95 mmol) in acetonitrile (4.0 mL) at room temperature was added iodotrimethysilane (0.2 mL, 0.125 mmol). The reaction mixture was stirred at 50° C. for 30 minutes, concentrated under reduced pressure and purified by flash chromatography with 2% methanol in dichloromethane to provide the titled compound. MS (CI) m/z 260 (M+1)+; 1H NMR (300 MHz, methanol-d4) δ ppm 8.31(d, 1H), 7.67 (d, d 1H), 6.87 (d, 1H), 4.83 (m, 2H), 3.79 (m, 2H), 3.63 (m, 2H), 1.63-1.54 (m, 4H), 1.22 (s, 3H).

Workup

concentrationconcentrated under reduced pressure
custompurified by flash chromatography with 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-97097edad6c44375a45b11e185e4712d
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262207B2

Reaction notes

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