Reaction #2028897

Reaction equation

(10-bromodecyl)phthalimide

triphenylphosphine

→

(10-aminodecyl)triphenylphosphonium bromide

10-decylphthalimidyl triphenylphosphonium bromide

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherprepared
2. 2
   Temperaturewas refluxed for 15 hours
3. 3
   workup.DISTILLATIONThe solvent distilled under reduced pressure
4. 4
   OtherPurification of the crude product by flash chromatography on a silica gel (CH2Cl2/EtOH 80:20)

Procedure

Both compounds, Mito-Gd-DOTA (FIG. 16-4) and Mito-Gd-DTPA, were synthesized according the synthetic route shown in FIG. 16. (10-aminodecyl)triphenylphosphonium bromide (FIG. 16-3) was synthesized and prepared as previously described. Briefly, a mixture containing (10-bromodecyl)phthalimide (7 g, 0.019 mol) and triphenylphosphine (5 g, 0.019 mol) in acetonitrile (60 mL) was refluxed for 15 hours. The solvent distilled under reduced pressure. Purification of the crude product by flash chromatography on a silica gel (CH2Cl2/EtOH 80:20) afforded a white solid 10-decylphthalimidyl triphenylphosphonium bromide (9 g, 73%). The calculated MS value for [C36H39NO2P]+, Br−; [C36H39NO2P]+ is 548.3. the product's MS value was 548.3. To prepare the (10-aminodecyl)triphenylphosphonium bromide (FIG. 16-3), hydrazine was added (0.54 mL, 0.0108 mol) to a solution of (10-decylphthalimidyl)triphenylphosphonium bromide (7 g, 0.0108 mol) in EtOH (70 mL). The mixture was refluxed for 15 hours. The solvent was removed under reduced pressure and the impurity was crystallized using a mixture Et2O/EtOH (100 mL+45 mL). The product was purified by flash chromatography on a silica gel (CH2Cl2/EtOH 80:20) afforded a yellow solid (4 g, 73%). The calculated HRMS for [C28H37NP]+, Br−; [C28H37NP]+ is 418.2. The product's measured HRMS value was 418.2.

Source