Hydrochloric Acid → HCID 86733863, compound

HRID 2397912Notes

Reaction equation

HRID 2397912 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([CH3:22])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:15])[C@@H:9]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)C1C=CC=CC=1.Cl.[H][H]>CN(C)C=O.[Pd]>[CH3:31][O:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C@H:9]2[C@@H:10]([C:14]([CH3:22])([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[OH:15])[CH2:11][CH2:12][CH2:13][NH:8]2)=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 86733862HCID 86733862, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86733863HCID 86733863, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 41.5 g. of cis-1-benzyl-2-(p-methoxybenzyl)-α-methyl-α-phenyl-3-piperidinemethanol in 8.3 ml. of concentrated hydrochloric acid is diluted with dimethylformamide to a volume of 400 ml. and catalytically hydrogenated under 10 atmospheres of hydrogen in the presence of palladium-on-carbon catalyst. The catalyst is removed by filtration and the solvent is evaporated from the filtrate under reduced pressure. The resulting residue is taken up in ethanol and diluted with diethyl ether to yield cis-2-(p-methoxybenzyl)-α-methyl-α-phenyl-3-piperidinemethanol.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated from the filtrate under reduced pressure
  3. additiondiluted with diethyl ether

Sources & evidence

ORD record
ord-1957798e093b4324a824a393261dc4f8
Source dataset
uspto-grants-1977_05
Patent number
US04022792

Reaction notes

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