Ammonium → HCID 18950754, compound

HRID 1492546Notes

Reaction equation

HRID 1492546 reaction equation
[NH4+].[CH3:2][O:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:14]#[N:15])=[CH:8][CH:7]=1>[Ni].CO>[CH3:2][O:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH:13]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][NH2:15])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 223AmmoniumHCID 18950697HCID 18950697, compound

Product 1

HCID 18950754HCID 18950754, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

An appropriate amount of Raney nickel was suspended in 30 ml of saturated solution of ammonium and methanol, followed by addition of 5.75 g of 3-(4-methoxymethyloxyphenyl)-2-(3-pyridyl)propionitrile, and stirred for 64 hours under 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 4.98 g of 3-(4-methoxymethyloxyphenyl)-2-(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-4b5e9362c6854700a61f03b645f64d55
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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