Hydrogen Bromide → HCID 86739449, compound

HRID 1381226Notes

Reaction equation

HRID 1381226 reaction equation
[CH3:1][C:2]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][C@@H:5]1[CH2:9][N:8](CC2C=CC=CC=2)[CH2:7][C@H:6]1[OH:17].[H][H].[BrH:25]>C(O)C.[Pd]>[BrH:25].[CH3:1][C:2]1[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:3]=1[O:4][C@@H:5]1[CH2:9][NH:8][CH2:7][C@H:6]1[OH:17]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 13320238HCID 13320238, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86739449HCID 86739449, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 9.1 g. (0.031 mole) of trans-4-(2,3-dimethylphenoxy)-1-phenylmethyl-3-pyrrolidinol in 100 liters of ethanol was hydrogenated over 10% palladium-on-charcoal at 50 psi and 60° C. until hydrogen uptake ceased. The mixture was filtered through Celite and the filtrate was concentrated to give an oil as residue which solidified upon standing. The solid was converted to the hydrobromide and this salt was recrystallized from isopropyl alcohol-ethylacetate-diethylether to yield 4.9 g (55%) of tan needles, m.p. 152°-3° C.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customto give an oil as residue which
  4. customthis salt was recrystallized from isopropyl alcohol-ethylacetate-diethylether

Sources & evidence

ORD record
ord-a77c47471bc9467a96ef76d0baa38924
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

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