Ethyl 4-piperidinecarboxylate → 1-[2-(4-Chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acid ethyl ester

HRID 638260Notes

Reaction equation

HRID 638260 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:3]=1.[NH:19]1[CH2:29][CH2:28][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]1>O.C(O)C>[CH2:26]([O:25][C:23]([CH:22]1[CH2:28][CH2:29][N:19]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:3]=2)[CH2:20][CH2:21]1)=[O:24])[CH3:27]

Participants

5

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 112195464-Chloro-2-(4-chlorophenyl)quinoline

Product 1

HCID 136039061-[2-(4-Chlorophenyl)-4-quinolinyl]-4-piperidinecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 10 g (36.4 mmol) of 4-chloro-2-(4-chlorophenyl)quinoline, and 20 ml of ethyl isonipecotate was stirred and heated at 160°-170° for 2 hr. It was then cooled and diluted with 200 ml of water and 5 ml of ethanol. The solid which formed was collected, and recrystallized from ethanol to give 5.5 g of product ester, mp 124°-126°.

Workup

  1. temperatureheated at 160°-170° for 2 hr
  2. temperatureIt was then cooled
  3. customThe solid which formed
  4. customwas collected
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2c80e1a098c842898d3693cb16fa0c10
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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