HCID 178475854, compound → HCID 178426529, compound

HRID 929658Notes

Reaction equation

HRID 929658 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]=1[CH2:8][NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=1)=[NH:11]>CO.[OH-].[OH-].[Pd+2]>[ClH:5].[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:10]([NH:9][CH2:8][C:7]2[CH:6]=[CH:23][CH:22]=[CH:21][C:20]=2[O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[NH:11])=[N:14][CH:15]=1

Participants

4

Reactant 1

HCID 178475854HCID 178475854, compound

Product 1

HCID 178426529HCID 178426529, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

0.111 g (0.261 mmol) N-(2-chloro-6-phenoxybenzyl)-N′-(5-methylpyridin-2-yl)guanidine acetate was dissolved in 10 mL methanol, and 10 mg Pearlman's catalyst (palladium hydroxide, 20% by weight Pd on C) was added. After evacuation and flushing of the reaction vessel with nitrogen, the reaction flask was re-evacuated and then filled with hydrogen. The reaction mixture was hydrogenated for 12 hr at room temperature. The catalyst was then separated via a membrane filter, and the resulting solution was removed from the solvent under vacuum. The viscous, clear residue was combined with diethyl ether, and after 2 hr crystallization 0.071 mg (0.192 mmol, 73%) purified N-(5-methylpyridin-2-yl)-N-(2-phenoxybenzyl) guanidine hydrochloride was isolated.

Workup

  1. customAfter evacuation and flushing of the reaction vessel with nitrogen
  2. customthe reaction flask was re-evacuated
  3. additionfilled with hydrogen
  4. customThe catalyst was then separated via a membrane
  5. filtrationfilter
  6. customthe resulting solution was removed from the solvent under vacuum
  7. customafter 2 hr crystallization 0.071 mg (0.192 mmol, 73%)
  8. custompurified N-(5-methylpyridin-2-yl)-N-(2-phenoxybenzyl) guanidine hydrochloride
  9. customwas isolated

Sources & evidence

ORD record
ord-724cb28675fb454b9a3de302b425718a
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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