Hydrochloric Acid → 1-(4-Quinolyl)-3-(4-piperidyl)-1-propanol

HRID 65216Notes

Reaction equation

HRID 65216 reaction equation
[BH4-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13](=[O:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1.Cl>CO>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([OH:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 202341131-(4-Quinolyl)-3-(4-piperidyl)-1-propanone

Product 1

HCID 155816751-(4-Quinolyl)-3-(4-piperidyl)-1-propanolYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 g of sodium borohydride were added in 20 minutes, at the ambient temperature, to 13 g of 1-(4-quinolyl)-3-(4-piperidyl)-1-propanone in 200 ml of methanol. After reacting for 2 hours at the ambient temperature, the reaction medium was acidified by addition of an aqueous solution of hydrochloric acid, the methanol removed by distillation under reduced pressure and the aqueous phase washed with ethyl acetate. The aqueous phase was made alkaline by addition of an aqueous solution of sodium hydroxide, then extracted with chloroform. The chloroformic phase was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. 13 g of crude product were thus obtained, which were fixed on a column of silica gel. It was then eluted with a mixture of 90 parts by volume of chloroform and 10 parts by volume of diethylamine. 7 g of the desired product were thus isolated in the form of the base, which was converted into dihydrochloride by the action of hydrochloric acid in ethanol. 3.2 g of 1 -(4-quinolyl)-3-(4-piperidyl)-1-propanol dihydrochloride (racemic) which melted at 195° C. were thus obtained.

Workup

  1. customthe methanol removed by distillation under reduced pressure
  2. washthe aqueous phase washed with ethyl acetate
  3. additionby addition of an aqueous solution of sodium hydroxide
  4. extractionextracted with chloroform
  5. washThe chloroformic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. custom13 g of crude product were thus obtained
  9. washIt was then eluted with a mixture of 90 parts by volume of chloroform and 10 parts by volume of diethylamine

Sources & evidence

ORD record
ord-3fe373b60696454d87f7681730255022
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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