Sodium Iodide → HCID 14098744, compound

HRID 620146Notes

Reaction equation

[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[CH2:15][C:14](=[O:16])[NH:13][C:12](=[O:17])[CH2:11]1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33]Cl)[CH2:27][CH2:26]2)=[CH:21][CH:20]=1.[I-].[Na+].N1C(=O)CNCC1=O>CN(C)C=O>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][N:10]1[CH2:15][C:14](=[O:16])[N:13]([CH2:33][CH2:32][CH2:31][N:28]2[CH2:29][CH2:30][N:25]([C:22]3[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=3)[CH2:26][CH2:27]2)[C:12](=[O:17])[CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 0.098 mole of sodium hydride in 30 ml of anhydrous dimethylformamide is heated to 60° C. A solution of 0.098 mole of 4-(2-pyridylmethyl)-2,6-piperazinedione in 15 ml of anhydrous dimethylformamide is added dropwise. When the addition is complete, the mixture is maintained at 60° C. for two hours. The reaction medium is then cooled to 25° C. and a solution of 0.126 mole of 4-(4-fluorophenyl)-1-(3-chloropropyl)piperazine in 10 ml of anhydrous dimethylformamide and 0.1 g of sodium iodide are added rapidly. The mixture is heated to 70° C. until the starting 2,6-piperazinedione has completely disappeared. The reaction medium is concentrated under vacuum. The solid residue is recrystallized in a mixture of iospropyl ether and ethanol (90:10). Pure crystals of 4-(2-pyridylmethyl)-1-{3-[1-(4-fluorophenyl)-4-piperazinyl]propyl}-2,6-piperazinedione are obtained.

Workup

additionWhen the addition
temperaturethe mixture is maintained at 60° C. for two hours
temperatureThe reaction medium is then cooled to 25° C.
concentrationThe reaction medium is concentrated under vacuum
customThe solid residue is recrystallized in a mixture of iospropyl ether and ethanol (90:10)

Sources & evidence

ORD record: ord-f0211a96b6194ac891fa2adc428419f0
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04820707

Reaction notes

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