HCID 21312549, compound → HCID 21312551, compound

HRID 971917Notes

Reaction equation

HRID 971917 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].C([N:14]1[CH2:19][CH2:18][C:17]([CH2:20][CH2:21][CH3:22])=[C:16]([CH3:23])[CH:15]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)C1C=CC=CC=1>[Pd].C(O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][CH:15]2[C:16]([CH3:23])=[C:17]([CH2:20][CH2:21][CH3:22])[CH2:18][CH2:19][NH:14]2)=[CH:30][CH:29]=1

Participants

4

Reactant 1

HCID 21312549HCID 21312549, compound

Product 1

HCID 21312551HCID 21312551, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-2-(p-methoxybenzyl)-3-methyl-4-propyl-1,2,5,6-tetrahydropyridine oxalate (377 g.), palladium-on-carbon (10%, 10.0 g.) and ethanol (to make 4,500 ml.) was hydrogenated for thirty minutes under pressure (about 50 p.s.i.g.), then filtered. The filtrate was concentrated, affording 2-(p-methoxybenzyl)-3-methyl-4-propyl-1,2,5,6-tetrahydropyridine oxalate in two crops (196 g. and 35 g.), which melted at 146°-147° C.

Workup

  1. waitwas hydrogenated for thirty minutes under pressure (about 50 p.s.i.g.)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-32ef23a3e18f43b2a4f1e013ae95bcd4
Source dataset
uspto-grants-1979_07
Patent number
US04161598

Reaction notes

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