4-(Trifluoromethyl)aniline → 1-(3-chloro-2-pyridinyl)-4-hydroxy-N-[4-(trifluoromethyl)phenyl]-4-piperidinecarboxamide

HRID 1246719Notes

Reaction equation

HRID 1246719 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][C:11]([OH:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CCN=C=NCCCN(C)C.[F:29][C:30]([F:39])([F:38])[C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][C:11]([OH:17])([C:14]([NH:35][C:34]3[CH:36]=[CH:37][C:31]([C:30]([F:29])([F:38])[F:39])=[CH:32][CH:33]=3)=[O:16])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 219047491-(3-Chloro-2-pyridinyl)-4-hydroxy-4-piperidinecarboxylic acid

Product 1

HCID 112465621-(3-chloro-2-pyridinyl)-4-hydroxy-N-[4-(trifluoromethyl)phenyl]-4-piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Chloro-2-pyridinyl)-4-hydroxy-4-piperidinecarboxylic acid, EDCI (525 mg, 2.7 mmol), and 4-(trifluoromethyl)aniline in dichloromethane (10 mL) were combined at room temperature and stirred overnight. Standard work-up gave a crude product which was purified via chromatography (SiO2, ethyl acetate:hexanes, 1:9). 1H NMR (500 MHz, CDCl3) δ 8.90 (s(br), 1H), 8.20 (dd, 1H), 7.74 (d, 2H), 7.61 (m, 3H), 6.86 (dd, 1H), 3.80 (m, 2H), 3.18 (m, 2H), 2.50 (m, 2H), 1.78 (m, 2H); MS (ESI, M+H)+400.

Workup

  1. customwere combined at room temperature

Sources & evidence

ORD record
ord-2aae64c9b2a248a190593ca137421949
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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