Benzyl Bromide → 1-Benzyl-tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione

HRID 15113

Reaction equation

HRID 15113 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC#N>[CH2:29]([N:1]1[C:5](=[O:6])[CH2:4][N:3]2[C:7](=[O:10])[CH2:8][CH2:9][CH:2]12)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 65955DimiracetamHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Product 1

HCID 112647151-Benzyl-tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tetrahydro-pyrrolo[1,2-a]imidazole-2,5-dione (0.5 g, 3.5 mmol, prepared as described in J. Med. Chem. 36, 4214, 1994), BEMP (2 ml, 7 mmol) and benzylbromide (0.6 ml, 5 mmol) in CH3CN (20 ml) was refluxed for 1 hour. The reaction mixture was concentrated to dryness; the residue was then re-dissolved in ethyl acetate and washed with a saturated solution of NaCl, dried over Na2SO4, filtered and evaporated under vacuum. The residue was purified by flash chromatography over silica gel (CH2Cl2/MeOH/NH4OH 95/5/0.5) to afford 0.7 g of the title compound as yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was then re-dissolved in ethyl acetate
  3. washwashed with a saturated solution of NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue was purified by flash chromatography over silica gel (CH2Cl2/MeOH/NH4OH 95/5/0.5)

Sources & evidence

ORD record
ord-63d0142ac98d4c76927d6b43eec7f446
Source dataset
uspto-grants-2010_06
Patent number
US07732473B2

Linked notes

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