HCID 86746022, compound → HCID 53783140, compound

HRID 654888Notes

Reaction equation

HRID 654888 reaction equation
C1(C[O:8][C:9]2[CH:34]=[CH:33][C:12]3[CH:13]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]([C:23]45[CH2:32][CH:27]6[CH2:28][CH:29]([CH2:31][CH:25]([CH2:26]6)[CH2:24]4)[CH2:30]5)=[O:22])[O:15][C:11]=3[CH:10]=2)C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:34]=[CH:33][C:12]2[CH:13]=[C:14]([CH2:16][NH:17][CH2:18][CH2:19][NH:20][C:21]([C:23]34[CH2:24][CH:25]5[CH2:31][CH:29]([CH2:28][CH:27]([CH2:26]5)[CH2:32]3)[CH2:30]4)=[O:22])[O:15][C:11]=2[CH:10]=1

Participants

4

Reactant 1

HCID 86746022HCID 86746022, compound

Product 1

HCID 53783140HCID 53783140, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[2-[[(6-Phenylmethoxy-2-benzofuranyl)methyl]amino]ethyl]tricyclo[3.3.1.13,7 ]decane-1-carboxamide (4.74 g, 10 mmole) was dissolved in 100 ml of ethanol and 1.0 g 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 column chromatographed on 100 g of silica gel using 5% methanol/chloroform as eluant and the crude product thus obtained was crystallized from 15 ml of ethanol with the addition of 8 ml of 4N HCl/isopropanol and 100 ml of diethyl ether to give 1.6 g of the title compound as a white solid, monohydrochloride, quarter hydrate, m.p. 136°-139° 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. customchromatographed on 100 g of silica gel using 5% methanol/chloroform as eluant
  5. customthe crude product thus obtained
  6. customwas crystallized from 15 ml of ethanol with the addition of 8 ml of 4N HCl/isopropanol and 100 ml of diethyl ether

Sources & evidence

ORD record
ord-2b0e1fe4d6e44adead387dee8653db01
Source dataset
uspto-grants-1992_07
Patent number
US05134140

Reaction notes

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