HCID 15952943, compound → N-[2-(3,5-Dichlorophenoxy)phenyl]piperidine-4-carboxamide
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:31])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][C:23]2[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[Cl:29][C:27]1[CH:28]=[C:23]([CH:24]=[C:25]([Cl:30])[CH:26]=1)[O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[NH:15][C:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)=[O:31]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
4-[2-(3,5-Dichloro-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (HVB01036, HVB01039 HVB01042, 1.09 g, 2.3 mmol) was dissolved in HCl/dioxane (4M, 18 ml), and stirred at room temperature for 1 h. The reaction mixture was evaporated to dryness, diluted with DCM (20 ml) and neutralised with sodium hydroxide (1M). Extracted with DCM, organic layers dried over anhydrous magnesium sulphate, and evaporated in-vacuo, 183 mg, 21%. m.p. 138-139° C., Rf. 0.3 (10% Methanol/DCM), 1HNMR (CDCl3, 270 MHz) δ 1.65 (3H, m, CH2 and NH), 1.86 (2H, m, CH2), 2.36 (1H, m, CH), 2.65 (2H, td, J=2.7, 9.6 Hz, NCH2), 3.16 (2H, m, NCH2), 6.89 (2H, d, J=1.7 Hz, ArHE, ArHG), 6.90 (1H, m, ArHD), 7.06 (1H, td, J=1.5, 7.4 Hz, ArHB), 7.12 (1H, t, J=1.7 Hz, ArHF), 7.18 (1H, td, J=8.2, 1.46 Hz, ArHC), 7.55 (1H, s, NH), 8.43 (1H, dd, J=8.2 Hz, ArHA).