HCID 15952943, compound → N-[2-(3,5-Dichlorophenoxy)phenyl]piperidine-4-carboxamide

HRID 1642208Notes

Reaction equation

HRID 1642208 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

HCID 15952943HCID 15952943, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

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).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with DCM (20 ml)
  3. extractionExtracted with DCM, organic layers
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in-vacuo, 183 mg, 21%

Sources & evidence

ORD record
ord-2c0a29fc082841d7b64446bfd51a4eed
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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