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Water → N-(2-(4-(Trifluoromethoxy)phenoxy)phenyl)piperidine-4-carboxamide

HRID 1642216
Notes
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Reaction equation

HRID 1642216 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 15952444HCID 15952444, compound

Product 1

HCID 57550283N-(2-(4-(Trifluoromethoxy)phenoxy)phenyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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

  1. additionadded
  2. extractionExtracted with DCM
  3. dry with materialthe organic layers dried over anhydrous magnesium sulphate
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes