HCID 21463006, compound → HCID 21462999, compound

HRID 1940573Notes

Reaction equation

HRID 1940573 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[Pt]=O>[O:1]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][NH:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21463006HCID 21463006, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21462999HCID 21462999, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 5-phenoxyisoquinoline (1 g, 4.5 mmol) in methanol (50 ml) was shaken on a Parr hydrogenator at 55 psi hydrogen in the presence of platinum oxide (0.2 g) for 3 h. The catalyst was then removed by filtration and the solvent evaporated. The residue was triturated with hexane to give the title compound as a colourless solid (0.6 g, 60%); δH (CDCl3) 2.65-2.75 (2H, m, ArCH2CH2N), 3.1-3.2 (2H, m, ArCH2CH2N), 4.05 (2H, br s, ArCH2N), 6.75 (1H, d, J 8 Hz, ArH), 6.83 (1H, d, J 8 Hz, ArH), and 6.9-7.35 (6H, m, ArH); m/z (CI+, NH3) 226 (M+1)+.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent evaporated
  3. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-3244b8a31a73484cac8a598ed0acf4d8
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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