Benzylamine → HCID 53629135, compound

HRID 1924222Notes

Reaction equation

HRID 1924222 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH:12]([CH2:14][CH2:15][CH3:16])[CH2:11][C:10]2=[O:17])=[CH:4][CH:3]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:18]([NH:25][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH:12]([CH2:14][CH2:15][CH3:16])[CH2:11][C:10]2=[O:17])=[CH:4][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 15979680HCID 15979680, compound

Product 1

HCID 53629135HCID 53629135, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-[(6-chloropyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 228 (100 mg, 0.396 mmol, 1 eq), benzylamine (65 μl, 0.61 mmol, 1.6 eq) and potassium carbonate (274 mg, 1.98 mmol, 5 eq) is added a stirred solution of Pd2(dba)3 (Tris(dibenzylideneacetone)dipalladium(0), 18 mg, 0.02 mol, 0.05 eq) and BINAP (13 mg, 0.02 mol, 0.05 eq) in 2 ml of 1,4-dioxane. The mixture is heated at reflux for 36 h, filtered and concentrated. The crude product is dissolved in water and extracted three times with CH2Cl2. The organic phase is dried over MgSO4, filtered and evaporated to dryness. The crude is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v)) to afford 14 mg of 1-{[6-(benzylamino)pyridin-3-yl]methyl}-4-propylpyrrolidin-2-one 229.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 36 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe crude product is dissolved in water
  6. extractionextracted three times with CH2Cl2
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v))

Sources & evidence

ORD record
ord-4997350b817f46809606b331ef5ccb19
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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