Hydrochloric Acid → HCID 86733863, compound

HRID 1283985Notes

Reaction equation

HRID 1283985 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 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-7f0a427c0d554c6fb1da8f17395f375c
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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