HCID 54037013, compound → HCID 53689594, compound

HRID 654887Notes

Reaction equation

HRID 654887 reaction equation
C1(C[O:8][C:9]2[CH:10]=[CH:11][C:12]3[O:16][C:15]([CH2:17][NH:18][CH2:19][CH2:20][NH:21][C:22]([C:24]45[CH2:33][CH:28]6[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]6)[CH2:25]4)[CH2:31]5)=[O:23])=[CH:14][C:13]=3[CH:34]=2)C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH2:17][NH:18][CH2:19][CH2:20][NH:21][C:22]([C:24]34[CH2:33][CH:28]5[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]5)[CH2:25]3)[CH2:31]4)=[O:23])=[CH:14][C:13]=2[CH:34]=1

Participants

4

Reactant 1

HCID 54037013HCID 54037013, compound

Product 1

HCID 53689594HCID 53689594, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-[[(5-Phenylmethoxy-2-benzofuranyl)methyl]amino]ethyl]tricyclo[3.3.1.13,7 ]decane-1-carboxamide (0.70 g, 1.5 mmole) was dissolved in 100 ml of ethanol and 160 mg of 10% palladium on carbon was added. The mixture was hydrogenated at 50 psi on a Parr apparatus overnight. The mixture was then filtered through celite and concentrated in vacuum. The residue was crystallized from 25 ml of isopropanol with the addition of 7 ml of 4N HCl/isopropanol and 100 ml of diethyl ether to give 320 mg of the title compound as a white solid, monohydrochloride, hydrate, m.p. 140°-143° C.

Workup

  1. customwas hydrogenated at 50 psi on a Parr apparatus overnight
  2. filtrationThe mixture was then filtered through celite and
  3. concentrationconcentrated in vacuum
  4. customThe residue was crystallized from 25 ml of isopropanol with the addition of 7 ml of 4N HCl/isopropanol and 100 ml of diethyl ether

Sources & evidence

ORD record
ord-fb200595fa5c4c19bf4012c56272b1d5
Source dataset
uspto-grants-1992_07
Patent number
US05134140

Reaction notes

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