Sodium Hydroxide → HCID 3062079, compound

HRID 2164594Notes

Reaction equation

HRID 2164594 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)=O)[CH2:3][CH2:2]1.O.NN.[OH-].[Na+]>C(O)COCCO.O>[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 3062061Ethanone, 2-(4-piperidinyl)-1-(4-quinolinyl)-

Product 1

HCID 3062079HCID 3062079, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 13 g of 2-(4-piperidyl)-1-(4-quinolyl)-ethanone, prepared as indicated in Example 1, and 10 ml of 98% hydrazine hydrate in 150 ml of diethylene glycol is heated at 180° C. for 2 hours. After cooling, 15 g of sodium hydroxide pellets are added and the mixture is kept at 180° C. for 18 hours. The reaction mixture is diluted with water, extracted with chloroform. The organic phase is washed with water, dried and evaporated under reduced pressure. 10 g of the desired product are obtained, which is converted into the hydrochloride by the action of hydrochloric acid in ethanol. 7.2 g of 4-[2-(4-piperidyl)-ethyl]-quinoline are obtained in the form of monohydrated dihydrochloride which melts at 210° C.

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1248c7c4111444eea4b5c5954815f4da
Source dataset
uspto-grants-1985_03
Patent number
US04505916

Reaction notes

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