2-Pyrrolidone → HCID 90001880, compound

HRID 1771393Notes

Reaction equation

HRID 1771393 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([I:17])[CH:12]=1>CN(C=O)C.O>[I:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

Participants

6

Reactant 3

HCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 27593613-Iodobenzyl bromide

Product 1

HCID 90001880HCID 90001880, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of pyrrolidin-2-one (1.55 mL, 20.2 mmol) in DMF (25 mL) at 0° C. under N2 was added NaH (60% dispersion in mineral oil, 808 mg, 20.2 mmol) portion-wise over 10 min. The reaction mixture was maintained at 0° C. for 30 min and was then treated with 1-(bromomethyl)-3-iodobenzene (5.00 g, 17.0 mmol) over 10 min and afterwards was warmed to RT for 2 hr. The resulting mixture was diluted with water (100 mL) and extracted with DCM (2×100 mL). The combined organic extracts were washed with water (100 mL) and with brine (100 mL) and evaporated in vacuo to afford 1-(3-iodobenzyl)pyrrolidin-2-one as a yellow oil (5.49 g, 100%); Rt 1.85 min (Method 2, acidic); m/z 302 (M+H)+, (ES+).

Workup

  1. temperatureafterwards was warmed to RT for 2 hr
  2. extractionextracted with DCM (2×100 mL)
  3. washThe combined organic extracts were washed with water (100 mL) and with brine (100 mL)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b68fc60c978e4664a25fc2322f9745bc
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

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