Bromomethyl 4-methoxyphenyl ketone → 2-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 1885583Notes

Reaction equation

HRID 1885583 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH:13]=[C:14]1[CH2:18][CH2:17][CH2:16][NH:15]1>C(Cl)(Cl)Cl>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:13]=[C:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:2]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 178507686HCID 178507686, compound

Product 1

HCID 9101232-(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 6.8 g (29.7 mmoles) of 2-bromo-4'-methoxyacetophenone in 50 ml of CHCl3 was added a solution of 5 g (59.4 mmoles) of 2-iminopyrrolidine in 30 ml of CHCl3 with chilling. After 4 hours of stirring at 25° C., the solvent was removed in vacuo. The residue was dissolved in water, the pH adjusted to 2.5 and the solution heated on a steam bath under argon atmosphere for 8 hours. The cooled solution was adjusted to pH 6. The resulting precipitate was filtered, washed with water and dried in vacuo to afford the titled compound, mp 116°-117° C.

Workup

  1. temperaturewith chilling
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. temperaturethe solution heated on a steam bath under argon atmosphere for 8 hours
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9b1ed7fdcf974da0a0bd0b1355ac4bdb
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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