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

HRID 580052Notes

Reaction equation

HRID 580052 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH2:11]Br)=O)=[CH:5][CH:4]=1.[NH:13]=[C:14]1[CH2:18][CH2:17][CH2:16][NH:15]1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:11]=2)=[CH:5][CH:4]=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, filtered, washed with water and dried in vacuo to afford the titled compound, mp 116°-117.5° 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, filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4d55958941954503b04830159e984ff1
Source dataset
uspto-grants-1988_06
Patent number
US04751310

Reaction notes

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