Water → HCID 18072498, Verbindung

To a stirred solution of 2-(trifluoromethyl)aniline (0.5 mL, 4.20 mmol) in dichloromethane (10.0 mL) was added 4-chlorocarbonylpiperidine-1-carboxylic acid tert-butyl ester (1.000 g, 4.00 mmol). The reaction mixture was stirred at ambient temperature for 10 minutes, then followed by the addition of triethylamine (0.6 mL, 4.20 mmol). The reaction mixture was stirred at ambient temperature for another 10 minutes. Water (5.0 mL) was added to the mixture and the organic phase separated and washed with saturated NaCl (10 mL), dried over MgSO4 and then concentrated in vacuo. The obtained crude product was purified by column chromatography to yield the desired product, 4-(2-trifluoromethylphenylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester, in 30% yield (0.450 g). 1H NMR (300 MHz, CDCl3) δ 7.97 (d, J=8.0 Hz, 1H), 7.61 (s. 1H), 7.53 (d, J=7.9 Hz, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.18 (t, J=7.6 Hz, 1H), 4.13-4.04 (m, 2H), 2.77-2.69 (m, 2H), 2.44-2.34 (m, 1H), 1.87-1.93 (m, 2H), 1.70-1.57 (m, 2H), 1.40 (s. 9H). MS (ES−) m/z 371 (M−1).

1. stirringThe reaction mixture was stirred at ambient temperature for another 10 minutes
2. customthe organic phase separated
3. washwashed with saturated NaCl (10 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe obtained crude product
7. customwas purified by column chromatography

ORD-Eintrag

ord-ff6c4261fef64993ba2e187e5e37bb15

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07951805B2