Sodium borohydride → cis-1-Methyl-3-phenyl-4-piperidinol

HRID 2163133Notes

Reaction equation

HRID 2163133 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5]1>O.CO>[CH3:3][N:4]1[CH2:9][CH2:8][C@H:7]([OH:10])[C@H:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 127885251-Methyl-3-phenylpiperidin-4-one

Product 1

HCID 12788379cis-1-Methyl-3-phenyl-4-piperidinol

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium borohydride (9.46 g) is added portionwise to a solution of the compound of formula IV, (-methyl-3-phenyl-4-piperidone (94.6 g, described by A. A. Patchett and F. F. Gianuso, supra), in water-methanol 1:9 (250 ml). The mixture is stirred for 30 minutes and the methanol is evaporated. The aqueous residue is diluted with water, 6N hydrochloric acid and washed with ether. The aqueous phase is made alkaline and extracted with chloroform. The chloroform extract is evaporated and crystallized from ether to give cis-1-methyl-3-phenyl-4-piperidinol, mp 131-133° C. Anhydrous hydrogen chloride is added to the mother liquors and the precipitate is crystallized from methanol-ether to give trans-1-methyl-3-phenyl-4-piperidnol hydrochloride, mp 131-133° C.

Workup

  1. customthe methanol is evaporated
  2. additionThe aqueous residue is diluted with water, 6N hydrochloric acid
  3. washwashed with ether
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customis evaporated
  7. customcrystallized from ether

Sources & evidence

ORD record
ord-dd784094465540cc892acd45dea32dbf
Source dataset
uspto-grants-1979_01
Patent number
US04132709

Reaction notes

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