Potassium borohydride → alpha-(1-Naphthyl)-4-piperidinemethanol

HRID 1389863Notes

Reaction equation

HRID 1389863 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[CH2:4][CH2:3]1.[BH4-].[K+]>CO>[C:10]1([CH:8]([CH:5]2[CH2:6][CH2:7][NH:2][CH2:3][CH2:4]2)[OH:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 202955361-Naphthyl 4-piperidyl ketone hydrochloride

Product 1

HCID 20295569alpha-(1-Naphthyl)-4-piperidinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 60 g (0.22 mole) of 1-naphthyl 4-piperidyl ketone hydrochloride in 500 ml of methanol, 35 g (0.65 mole) of potassium borohydride is added gradually while stirred in an ice bath and the mixture reacted for 18 hours. The mixture is concentrated in vacuo, the residue partitioned between chloroform and water, and the organic phase dried over magnesium sulfate, filtered and the solvent removed in vacuo to yield α-(1-naphthyl)-4-piperidinemethanol, which is dissolved in chloroform and an excess of dry HCl bubbled into the solution. The resulting precipitate is recrystallized from methanol/butanone to yield α-(1-naphthyl)-4-piperidinemethanol hydrochloride. M.P. 219°-21°.

Workup

  1. customthe mixture reacted for 18 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe residue partitioned between chloroform and water
  4. dry with materialthe organic phase dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-84599ad969f54bf0b7b9064d30ac9cad
Source dataset
uspto-grants-1981_01
Patent number
US04246268

Reaction notes

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