Sodium Carbonate → 2-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 1885593

Reaction equation

Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.Cl.[NH:13]=[C:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[N:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:13]=[C:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:3]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 10 g (35.6 mmoles) of 4-(bromoacetyl)-pyridine hydrobromide and 12.9 g (107 mmoles) of 2-imino-pyrrolidine hydrochloride in 100 ml of dry dimethylformamide was treated with 18.9 g (178 mmoles) of anhydrous sodium carbonate. This suspension was heated at 80° C. overnight in an oil bath. The solvent was removed in vacuo, the residue dissolved in water and extracted with chloroform. The organic layer was washed three times with water, dried over anhydrous potassium carbonate and stripped in vacuo. The residue was chromatographed on silica and eluted with 10-15% methanol in methylene chloride acetone (85:15). This fraction was stripped in vacuo and the solid residue recrystallized twice from ethyl acetate to afford the desired titled compound, mp 140°-141° C., 1HNMR (250 MHz, CDCl3) δ 8.62 (2H,d), 7.60(2H,d), 7.34(1H,s), 4.04(2H,t), 2.95 (2H,t), 2.64(2H,q).

Workup

customThe solvent was removed in vacuo
dissolutionthe residue dissolved in water
extractionextracted with chloroform
washThe organic layer was washed three times with water
dry with materialdried over anhydrous potassium carbonate
customThe residue was chromatographed on silica
washeluted with 10-15% methanol in methylene chloride acetone (85:15)
customthe solid residue recrystallized twice from ethyl acetate

Sources & evidence

ORD record: ord-57ee2631cd574db8af1c8fd9ab36138d
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05145858

Linked notes

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