Water → HCID 3075781, compound

HRID 1995759Notes

Reaction equation

HRID 1995759 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26](OCC)=O)[CH2:22][CH2:21]1)=[CH:15][C:14]([O:31][CH3:32])=[CH:13][CH:12]=2.O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1)=[CH:15][C:14]([O:31][CH3:32])=[CH:13][CH:12]=2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20431846HCID 20431846, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3075781HCID 3075781, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

0.38 g of lithium aluminum hydride are introduced progressively and portionwise into 20 ml of dry tetrahydrofuran, under an atmosphere of nitrogen. The suspension obtained is cooled to 0° C., then a solution of 1.6 g of 3-chloro-6-methoxy-4-[2-(1-ethoxycarbonyl-4-piperidyl)-ethyl]-quinoline in tetrahydrofuran is added drop by drop. The reaction medium is maintained for 3 hours in an ice bath, then 0.45 ml of water, 0.33 ml of a 5 N aqueous solution of sodium hydroxide and 15 ml of water are added, very slowly and in the order given. The insoluble mineral products formed are separated by filtration and washed twice with 30 ml of methylene chloride. The filtrate and the washings are collected, dried over magnesium sulfate, then concentrated by evaporation. The residue obtained is fixed on a column of silica and eluted with a 90/10 mixture of chloroform and diethylamine. 0.9 g of 3-chloro-6-methoxy-4-[2-(1-methyl-4-piperidyl)-ethyl]-quinoline are thus obtained, the hydrochloride of which is amorphous.

Workup

  1. customThe suspension obtained
  2. temperatureThe reaction medium is maintained for 3 hours in an ice bath
  3. customThe insoluble mineral products formed
  4. customare separated by filtration
  5. washwashed twice with 30 ml of methylene chloride
  6. customThe filtrate and the washings are collected
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe residue obtained
  10. washeluted with a 90/10 mixture of chloroform and diethylamine

Sources & evidence

ORD record
ord-50b7686baa7e4668a2f1c6b1737a7785
Source dataset
uspto-grants-1983_09
Patent number
US04405789

Reaction notes

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