HCID 18950663, compound → HCID 18950687, compound

HRID 1492540Notes

Reaction equation

HRID 1492540 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[C:12]#[N:13])=[CH:7][CH:6]=1>[Ni].CO.[H][H]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:12][NH2:13])=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 18950663HCID 18950663, compound

Product 1

HCID 18950687HCID 18950687, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

An appropriate amount of Raney nickel was suspended in 30 ml of saturated ammonical methanol solution, followed by addition of 3.81 g of 2-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)propionitrile, and stirred for 72 hours in hydrogen atmosphere of 15 atm. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, which was then eluted with aqueous ammonia-methanol-chloroform (1:10:100 v/v), and from the eluted fraction was obtained 3.27 g of 2-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)propylamine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. washwas then eluted with aqueous ammonia-methanol-chloroform (1:10:100 v/v)

Sources & evidence

ORD record
ord-65419a9ab5a44e6098fcf5c4c91e4f75
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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