Trifluoroacetic acid → N-[2-(3,5-Dichlorophenoxy)phenyl]piperidine-4-carboxamide

HRID 1642221Notes

Reaction equation

HRID 1642221 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.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 15952943HCID 15952943, compound

Product 1

HCID 57550316N-[2-(3,5-Dichlorophenoxy)phenyl]piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[2-(3,5-Dichloro-phenoxy)-phenylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (036 g, 0.77 mmol) was dissolved in DCM (9 ml), and to this was added TFA (4 ml). The reaction was stirred at room temperature for 2 h. This was then poured onto solid K2CO3, and extracted using DCM and water, to afford the desired product as a yellow solid. 0.21 g, (75%), 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, NCH2), 3.16 (2H, m, NCH2), 6.89 (2H, d, J=1.7, HE, HG), 6.90 (1H, m, HD), 7.06 (1H, td, J=1.5, 7.4, HB), 7.12 (1H, t, J=1.7, HF), 7.18 (1H, td, J=8.2, 1.46, HC), 7.55 (1H, s, NH), 8.43 (1H, dd, J=8.2, HA).

Workup

  1. extractionextracted

Sources & evidence

ORD record
ord-6cb7469517a34349b35cfaa0473997cd
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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