Benzamidine → HCID 178514988, compound

HRID 2249604Notes

Reaction equation

Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=[O:17].[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:20]1([C:19]2[NH:26][CH:2]=[C:3]([CH2:4][CH2:5][CH2:6][N:7]3[C:15](=[O:16])[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]3=[O:17])[N:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(5-bromo-4-oxo-pentyl)-isoindole-1,3-dione [CAS 41306-64-3](12.4 g) in abs. DMF (50 ml) was added benzamidine 85% (5.65 g) and potassium carbonate (11.05 g). The reaction mixture was stirred at 80° C. for 4 h, concentrated under high vacuum, quenched with water and extracted with ethyl acetate. The organic phase was washed with ice/water and brine, dried over magnesium sulphate and concentrated. The residue was purified by chromatography on silica gel using methylene chloride/methanol 2 and 5% as eluent. The product fractions were combined and evaporated to dryness to obtain 2-[3-(2-phenyl-1H-imidazol-4-yl)-propyl]-isoindole-1,3-dione (8.95 g) as a light yellow foam.

Workup

concentrationconcentrated under high vacuum
customquenched with water
extractionextracted with ethyl acetate
washThe organic phase was washed with ice/water and brine
dry with materialdried over magnesium sulphate
concentrationconcentrated
customThe residue was purified by chromatography on silica gel
customevaporated to dryness

Sources & evidence

ORD record: ord-2c2143e804204ea7acec69877a851e6f
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314884B2

Reaction notes

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