Ethyl chloroformate → 4-[2-(1-Ethoxycarbonyl-4-piperidyl)-ethyl]-2-phenyl quinoline

HRID 1388799Notes

Reaction equation

HRID 1388799 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([CH2:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(Cl)(Cl)Cl>[CH2:31]([O:30][C:28]([N:22]1[CH2:23][CH2:24][CH:19]([CH2:18][CH2:17][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:16]=2)[CH2:20][CH2:21]1)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 712192-Phenyl-4-(2-(4-piperidinyl)ethyl)quinoline

Product 1

HCID 129027164-[2-(1-Ethoxycarbonyl-4-piperidyl)-ethyl]-2-phenyl quinolineYield 104.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 15.6 g of 2-phenyl-4-[2-(4-piperidyl)ethyl] quinoline, prepared as indicated in Example 16, in 200 ml of chloroform is treated with stirring with 200 ml of a 1 N aqueous solution of sodium hydroxide. Then 21.7 g of ethyl chloroformate are added, drop by drop, and the suspension obtained is stirred for 17 hours at the ambient temperature. After separation, the organic phase is washed with water, dried over magnesium sulphate, then evaporated under reduced pressure. 20 g of 4-[2-(1-ethoxycarbonyl-4-piperidyl)-ethyl]-2-phenyl-quinoline in the form of an oil are obtained.

Workup

  1. additionis treated
  2. customdrop by drop, and the suspension obtained
  3. customAfter separation
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c3cd7fb62a2248498830bd2da72062c1
Source dataset
uspto-grants-1984_02
Patent number
US04433150

Reaction notes

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