Potassium Carbonate → HCID 58911267, compound

HRID 1295809Notes

Reaction equation

HRID 1295809 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:10][CH2:9]1)=[O:6].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:11]1([C:8]2([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])[CH2:10][CH2:9]2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58911254HCID 58911254, compound

Product 1

HCID 58911267HCID 58911267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, the crude 4-bromo-N-(l-imidazol-1-yl-cyclopropyl)-butyramide a18 (2.76 g), K2CO3 (1.26 g, 9.1 mmol) and KI (0.0075 g) in DMF (25 ml) are heated 3 h at 60° C., 17 h at 80° C., cooled down to room temperature and concentrated in vacuo. The reaction mixture is diluted with CH2Cl2, filtered and concentrated in vacuo to give the crude pyrrolidone (1.7 g). The residue is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 95/4.5/05 (v/v/v)) to give, after treatment with HCl in ether (1 eq) and recrystallization in MeCN, 1-[l-(1H-imidazol-1-yl)cyclopropyl]pyrrolidin-2-one 23 (0.033 g, 7.5%) as an hydrochloride.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe reaction mixture is diluted with CH2Cl2
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52b10fa113b44a2c9e20d5600c7ee7ba
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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