Potassium Iodide → HCID 13505770, compound

HRID 464250Notes

Reaction equation

HRID 464250 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[N:12]2[C:7]([CH2:8][O:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=32)=[N:6]1.[I-].[K+].[C:21]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[C:21]1([N:27]2[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][N:5]3[C:13](=[O:14])[N:12]4[C:7]([CH2:8][O:9][C:10]5[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=54)=[N:6]3)[CH2:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 13505766HCID 13505766, compound

Product 1

HCID 13505770HCID 13505770, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.32 g. (0.005 mole) of 2-(3-chloropropyl)2,4-dihydro-1H-[1,2,4]triazolo[3,4-c][1,4]benzoxazin-1-one in 25 ml. of dry DMF was treated with 0.83 g. (0.005 mole) of potassium iodide and 1.78 g. (0.011 mole) of N-phenylpiperazine. The resulting mixture was kept at 50° C. for 18 hours, at 85° C. for 2 hours and at 105° C. for 2.5 hours. The mixture was then cooled, poured into ice water and extracted with methylene chloride. The methylene chloride extracts were combined, washed with dilute brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was chromatographed on 125 g. of silica gel and eluted therefrom with a 1.5% v/v methanol in chloroform mixture. The eluted product was crystallized in the manner described in example 1, hereinabove, from an ethyl acetate/Skellysolve®B hexane mixture to give in two crops 0.74 g., m.p. 95°-96.5° C., and 0.37 g., m.p. 94°-96° C. of the titled compound. The analytical sample has a melting point of 96°-96.5° C.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with methylene chloride
  3. washwashed with dilute brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was chromatographed on 125 g
  7. washof silica gel and eluted
  8. customThe eluted product was crystallized in the manner
  9. customto give in two crops 0.74 g

Sources & evidence

ORD record
ord-c9d437ec58d0464090a75cd8051254cd
Source dataset
uspto-grants-1985_10
Patent number
US04547499

Reaction notes

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