Water → 4-[2-(1-Methyl-4-Piperidyl)-Ethyl]-2-Phenyl-Quinoline

HRID 2164600Notes

Reaction equation

HRID 2164600 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=2)[CH2:14][CH2:13]1)=O)C.O.[OH-].[Na+]>O1CCCC1>[CH3:10][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 129027164-[2-(1-Ethoxycarbonyl-4-piperidyl)-ethyl]-2-phenyl quinolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 30317534-[2-(1-Methyl-4-Piperidyl)-Ethyl]-2-Phenyl-Quinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g of lithium aluminum hydride are progressively introduced, incrementally, in 200 ml of dry tetrahydrofuran, under an atmosphere of nitrogen. The suspension obtained is cooled to 0° C., then a solution of 20 g of 4-[2-(1-ethoxycarbonyl-4-piperidyl)-ethyl]-2-phenyl quinoline in 200 ml of tetrahydrofuran is added drop by drop, the temperature of the reaction mixture being maintained below 30° C. After 4 hours of contact at the ambient temperature, there are introduced very slowly and successively 5.85 ml of water, 4.3 ml of a 5N aqueous solution of sodium hydroxide, then 19.5 ml of water. The mineral products are separated by filtration and washed twice with 30 ml of methylene chloride each time. The filtrates are collected, dried over magnesium sulphate, then evaporated to dryness. The residue obtained, which is constituted by the desired product, is acidified with the equivalent quantity of a solution of hydrochloric acid in ethanol. 11.1 g of 4-[2-(1-methyl- 4-piperidyl)-ethyl]-2-phenyl quinoline in the form of monohydrochloride melting at 206° C. are obtained.

Workup

  1. customThe suspension obtained
  2. temperaturethe temperature of the reaction mixture being maintained below 30° C
  3. additionAfter 4 hours of contact at the ambient temperature, there are introduced very slowly
  4. customThe mineral products are separated by filtration
  5. washwashed twice with 30 ml of methylene chloride each time
  6. customThe filtrates are collected
  7. dry with materialdried over magnesium sulphate
  8. customevaporated to dryness
  9. customThe residue obtained

Sources & evidence

ORD record
ord-9b87eb657daf4307bdf84f9f2bb3f325
Source dataset
uspto-grants-1985_03
Patent number
US04505916

Reaction notes

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