Potassium Iodide → 3-[2-[4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]-6-nitro-2,4(1H,3H)-quinazolinedione

HRID 978447Notes

Reaction equation

HRID 978447 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=2)[NH:6][C:5]1=[O:18].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[O:30][CH2:29][CH2:28][O:27]2)=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+].[I-].[K+]>CN(C)C=O>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH:31]3[CH2:36][CH2:35][N:34]([CH2:2][CH2:3][N:4]4[C:13](=[O:14])[C:12]5[C:7](=[CH:8][CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=5)[NH:6][C:5]4=[O:18])[CH2:33][CH2:32]3)[O:30][CH2:29][CH2:28][O:27]2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 132790992-(4-Fluorophenyl)-2-(4-piperidyl)1,3-dioxolaneHCID 138512013-(2-chloroethyl)-6-nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 138511763-[2-[4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]-6-nitro-2,4(1H,3H)-quinazolinedioneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 16.2 parts of 3-(2-chloroethyl)-6-nitro-2,4(1H,3H)-quinazolinedione, 15 parts of 4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]piperidine, 10 parts of sodium hydrogen carbonate, 0.1 parts of potassium iodide and 135 parts of N,N-dimethylformamide was stirred and heated overnight at 100°-120° C. The reaction mixture was cooled and poured onto water. Stirring was continued till complete precipitation. The precipitate was filtered off and dissolved in trichloromethane. The thus formed emulsion was dried, filtered and evaporated. The residue was crystallized from acetonitrile, yielding 18.6 parts (64%) of 3-[2-[4-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]-6-nitro-2,4(1H,3H)-quinazolinedione; mp. 250.9° C. (28).

Workup

  1. temperatureheated overnight at 100°-120° C
  2. temperatureThe reaction mixture was cooled
  3. additionpoured onto water
  4. stirringStirring
  5. customwas continued till complete precipitation
  6. filtrationThe precipitate was filtered off
  7. dissolutiondissolved in trichloromethane
  8. customThe thus formed emulsion was dried
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-43552f0949b54fb39d4a1931feba9fd7
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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