Acetonitrile → HCID 58761682, compound

HRID 857834Notes

Reaction equation

HRID 857834 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[N:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[Pd:23]([Cl:25])[Cl:24].CC#N>C1COCC1>[Pd:23]([Cl:25])[Cl:24].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[N:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[N:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24290Palladium ChlorideHCID 100629331-(pyridin-2-yl)-N-[(1R,2R)-2-{[(pyridin-2-yl)methylidene]amino}cyclohexyl]methanimine

Product 1

HCID 58761682HCID 58761682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a baked Schlenk tube, 1.0 g (3.4 mmol) of trans-N,N′-bispyridin-2-ylmethylenecyclohexane-1,2-diamine are dissolved in 40 ml of THF and admixed with 882 mg (3.4 mmol) of palladium(II) chloride*2 CH3CN. After 0.2 h, the solution becomes yellowish. After stirring at room temperature for another 2 hours, the solvent is removed under reduced pressure and the residue is stirred with 10 ml of heptane. Filtration through a G3 frit gives the product as a yellow solid in a yield of 1.45 g (2.92 mmol, 86%).

Workup

  1. customthe solvent is removed under reduced pressure
  2. stirringthe residue is stirred with 10 ml of heptane
  3. filtrationFiltration through a G3 frit

Sources & evidence

ORD record
ord-af3080feb9cb4e44a94d87e18c41d0d3
Source dataset
uspto-grants-2006_12
Patent number
US07148174B2

Reaction notes

Loading…