Water → 1-(2-Phenyl-4-quinolyl)-2-(4-piperidyl)-ethanol

HRID 65215Notes

Reaction equation

HRID 65215 reaction equation
[BH4-].[Na+].Cl.Cl.[C:5]1([C:11]2[CH:20]=[C:19]([C:21](=[O:29])[CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[C:5]1([C:11]2[CH:20]=[C:19]([CH:21]([OH:29])[CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3062066Ethanone, 1-(2-phenyl-4-quinolinyl)-2-(4-piperidinyl)-, dihydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 130752861-(2-Phenyl-4-quinolyl)-2-(4-piperidyl)-ethanolYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6 g of sodium borohydride were added in 20 minutes, at the ambient temperature, to 16 g of 1-(2-phenyl-4-quinolyl)-2-(4-piperidyl)-ethanone dihydrochloride in 500 ml of methanol. After reacting for 2 hours at the ambient temperature, 350 ml of water were added and the methanol was removed by distillation under reduced pressure. The residual aqueous suspension was extracted with diethyl oxide, the organic phase was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue (13 g) was crystallized from petrol ether. 9 g of 1-(2-phenyl-4-quinolyl)-2-(4-piperidyl)-ethanol (racemic) were thus obtained, which melted at 147° C.

Workup

  1. additionwere added
  2. customthe methanol was removed by distillation under reduced pressure
  3. extractionThe residual aqueous suspension was extracted with diethyl oxide
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue (13 g) was crystallized from petrol ether

Sources & evidence

ORD record
ord-db24660f31824cc49a9e83123a20e0f4
Source dataset
uspto-grants-1986_09
Patent number
US04613607

Reaction notes

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