Chlorosuccinimide → HCID 57743079, compound

HRID 1926768Notes

Reaction equation

HRID 1926768 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]2=[O:15])[N:3]=[CH:2]1.[Cl:16]N1C(=O)CCC1=O>CC#N.C1COCC1>[Cl:16][C:5]1[N:1]=[CH:2][NH:3][C:4]=1[CH2:6][N:7]1[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]1=[O:15]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178439462HCID 178439462, compound

Product 1

HCID 57743079HCID 57743079, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 ml, three-necked flask fitted with a magnetic stirrer and under inert atmosphere, 1-(1H-imidazol-4-ylmethyl)-4-propylpyrrolidin-2-one 110 (500 mg, 2.4 mmol) is dissolved in a 1/1 mixture of CH3CN/THF (40 ml) and the solution is cooled to 0° C. N-chlorosuccinimide (410 mg, 3.1 mmol) is added by portions while the temperature is maintained at 0° C. The mixture is stirred for 18 h at this temperature. Most of the solvents are removed under vacuum and the residue is dissolved in 1N HCl and diluted with CH2Cl2. The first organic phase is removed and pH of the aqueous phase is adjusted to 9 by addition of solid Na2CO3. Then CH2Cl2 is added and the second organic phase is separated, dried over MgSO4 and concentrated to dryness. Purification by preparative chromatography on silicagel (eluent: CH2Cl2/MeOH/NH4OH: 95/05/0.5 (v/v/v)) affords 440 mg of 1-[(4-chloro-1H-imidazol-5-yl)methyl]-4-propylpyrrolidin-2-one 126.

Workup

  1. temperatureis maintained at 0° C
  2. customMost of the solvents are removed under vacuum
  3. dissolutionthe residue is dissolved in 1N HCl
  4. additiondiluted with CH2Cl2
  5. customThe first organic phase is removed
  6. additionpH of the aqueous phase is adjusted to 9 by addition of solid Na2CO3
  7. additionThen CH2Cl2 is added
  8. customthe second organic phase is separated
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated to dryness
  11. customPurification by preparative chromatography on silicagel (eluent: CH2Cl2/MeOH/NH4OH: 95/05/0.5 (v/v/v))

Sources & evidence

ORD record
ord-858e9f2a7754441291226a4f2b848a08
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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