Water → N-[2-(2,4-Dichlorophenoxy)phenyl]piperidine-4-carboxamide

HRID 1642214Notes

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]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[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.CCOC(C)=O>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=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

Conditions

Temperature: 0 °C

Procedure

4-[2-(2,4-Dichloro-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (AMR01046, 1.0 g, 2.15 mmol) was dissolved in DCM (20 ml), and cooled to 0° C. and to this was added TFA (5 ml). This was allowed to warm to room temperature and stirred for 30 min. The reaction mixture was poured onto solid potassium carbonate (12 g), and water (50 ml) added. Extracted with DCM and the organic layers dried over anhydrous magnesium sulphate, and evaporated in-vacuo, to afford a cream oil, 0.77 g, 98%. R.f. 0.2 (EtOAc) 1HNMR (CDCl3, 300 MHz) δ 1.72 (2H, m, CH2), 1.87 (2H, m, CH2), 2.39 (1H, m, CH), 2.68 (2H, td, J=2.7, 12.3 Hz, CH2), 3.16 (2H, dt, J=3.6, 7.2, 12.6 Hz, CH2), 6.66 (1H, dd, J=1.5, 8.1 Hz, ArH), 6.87 (1H, d, J=8.7 Hz, ArH), 6.94 (1H, td, J=1.8, 8.1 Hz, ArH), 7.07 (1H, td, J=1.2, 7.8 Hz, ArH), 7.15 (1H, dd, J=2.7, 9.0 Hz, ArH), 7.43 (1H, d, J=2.4 Hz, ArH), 8.34 (1H, dd, J=6.9 Hz, ArH).

Workup

temperatureto warm to room temperature
additionadded
extractionExtracted with DCM
dry with materialthe organic layers dried over anhydrous magnesium sulphate
customevaporated in-vacuo
customto afford a cream oil, 0.77 g, 98%

Sources & evidence

ORD record: ord-ba497996cc6245ec80971258839ca8a9
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119627B2

Reaction notes

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