Water → N-{2-[4-(Trifluoromethoxy)phenoxy]phenyl}piperidine-4-carboxamide

HRID 1642216Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:34])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)Cl>[F:32][C:30]([F:31])([F:33])[O:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:34])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-[2-(4-Trifluoromethoxy-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (HVB01064, 0.3 g, 0.62 mmol) was dissolved in anhydrous DCM (7 ml), cooled to 0° C. and to this was added TFA (2.8 ml), and the reaction mixture was stirred under nitrogen for 1.5 h. The reaction mixture was poured onto solid potassium carbonate (6 g), and water (25 ml) added. Extracted with DCM and the organic layers dried over anhydrous magnesium sulphate, and evaporated in-vacuo, 0.21 g, 87%. Rf: 0.35 (DCM), 1HNMR: (CDCl3, 270 MHz) δ 1.64 (2H, m, CH2), 1.79 (2H, dd, J=2.7, 12.9 Hz, CH2), 2.32 (1H, m, CH), 2.61 (2H, td, J=2.7, 12.3 Hz, NCH2), 2.94 (1H, s, NH), 3.10 (2H, td, J=3.3, 12.6 Hz, NCH2), 6.79 (1H, dd, J=1.2, 8.1, ArHD), 6.95 (2H, m, ArHE), 6.95 (1H, m, ArHE), 7.08 (1H, td, J=1.5, 7.8 Hz, ArHc), 7.13 (2H, d, J=8.4 Hz, ArHF), 7.62 (1H, s, NH), 8.34 (1H, dd, J=1.2, 8.1 Hz, ArHA).

Workup

additionadded
extractionExtracted with DCM
dry with materialthe organic layers dried over anhydrous magnesium sulphate
customevaporated in-vacuo, 0.21 g, 87%

Sources & evidence

ORD record: ord-0b729bc57d2b49dcaf0d5b23cd123354
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119627B2

Reaction notes

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