Sodium hydride → HCID 15979680, compound

HRID 1896358Notes

Reaction equation

HRID 1896358 reaction equation
[CH2:1]([CH:4]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5]1)[CH2:2][CH3:3].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][N:12]=1.[H-].[Na+]>C(#N)C>[Cl:10][C:11]1[N:12]=[CH:13][C:14]([CH2:17][N:7]2[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]2=[O:9])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 141781004-Propylpyrrolidin-2-one

Product 1

HCID 15979680HCID 15979680, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4-propylpyrrolidin-2-one x1 (0.50 g, 3.93 mmol, 1 eq) and 2-chloro-5-(chloromethyl)pyridine x37 (0.64 g, 3.93 mmol, 1 eq) in acetonitrile (3 ml) is heated at 50° C. NaH (60% dispersion in oil, 158 mg, 3.93 mmol, 1 eq) and acetonitrile (5 ml) are added and the solution is stirred for 8 h at 50° C. The mixture is then poured on ice/water and the aqueous phase is extracted with CH2Cl2. The combined organic phases are dried over MgSO4, filtered and concentrated to dryness. The crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 99/1/0.1 (v/v/v)) to afford 790 mg of 1-[(6-chloropyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 228.

Workup

  1. additionThe mixture is then poured on ice/water
  2. extractionthe aqueous phase is extracted with CH2Cl2
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 99/1/0.1 (v/v/v))

Sources & evidence

ORD record
ord-3703d628ae6048b798f27ba30ed2c964
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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