4-Chloro-7-(trifluoromethyl)quinoline → 4-[(4-Fluorophenyl)hydroxymethyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine hydrochloride

HRID 648510Notes

Reaction equation

HRID 648510 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:39]=[CH:38][C:20]([C:21]([N:23]2[CH2:28][CH2:27][CH:26]([CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])[CH2:25][CH2:24]2)=[O:22])=[CH:19][CH:18]=1>C(O)C>[ClH:1].[F:37][C:34]1[CH:33]=[CH:32][C:31]([CH:29]([OH:30])[CH:26]2[CH2:27][CH2:28][N:23]([C:21](=[O:22])[C:20]3[CH:19]=[CH:18][C:17]([NH:16][C:2]4[C:11]5[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=5)[N:5]=[CH:4][CH:3]=4)=[CH:39][CH:38]=3)[CH2:24][CH2:25]2)=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 138250431-(4-Aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidine

Product 1

HCID 201449314-[(4-Fluorophenyl)hydroxymethyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine hydrochlorideYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-7-(trifluoromethyl)quinoline (0.32 g) and 1-(4-aminobenzoyl)-4-[(4-fluorophenyl)hydroxymethyl]piperidine (0.45 g) in dry ethanol (10 ml) was stirred under reflux for 4 hours and concentrated to dryness in vacuo. The residue was recrystallized from a mixture of ethyl acetate and isopropanol to give 4-[(4-fluorophenyl)hydroxymethyl]-1-[4-[[7-(trifluoromethyl)-4-quinolyl]amino]benzoyl]piperidine hydrochloride (0.65 g) as pale yellow powder.

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated to dryness in vacuo
  3. customThe residue was recrystallized from a mixture of ethyl acetate and isopropanol

Sources & evidence

ORD record
ord-2bd6b18266c1413c914439e2c3b555d6
Source dataset
uspto-grants-1988_04
Patent number
US04735952

Reaction notes

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