Potassium Iodide → HCID 13505768, compound

HRID 464251Notes

Reaction equation

HRID 464251 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[N:13]2[C:8]([CH2:9][O:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=32)=[N:7]1.[I-].[K+].[O:22]=[C:23]1[N:27]([CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:26]2[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=2[NH:24]1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[O:22]=[C:23]1[N:27]([CH:28]2[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:14](=[O:15])[N:13]4[C:8]([CH2:9][O:10][C:11]5[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=54)=[N:7]3)[CH2:32][CH2:33]2)[C:26]2[CH:34]=[CH:35][CH:36]=[CH:37][C:25]=2[NH:24]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 516892Sodium BicarbonateHCID 13505775HCID 13505775, compound

Product 1

HCID 13505768HCID 13505768, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-chlorobutyl)-2,4-dihydro-1H-[1,2,4]triazolo[3,4-c][1,4]benzoxazin-1-one, (1.40 g., 0.005 mole), potassium iodide (0.83 g.; 0.005 mole) and 4-(2-keto-1-benzimidazolinyl)piperidine (2.39 g.; 0.011 mole) in 25 ml. of DMF was warmed to 115° C. and stirred for 4.75 hours. The resulting solution was cooled, poured into saturated sodium bicarbonate aqueous solution and extracted with methylene chloride. The methylene chloride extracts were combined and washed with brine solution, dried over sodium sulfate and concentrated in vacuo. The resulting residue was crystallized from ethyl acetate to give 1.87 g., m.p. 173°-175.5° C. and 0.03 g., m.p. 172°-173° C. of the above named end product. The analytical sample had melting point 174°-175.5° C.

Workup

  1. temperatureThe resulting solution was cooled
  2. extractionextracted with methylene chloride
  3. washwashed with brine solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was crystallized from ethyl acetate
  7. customto give 1.87 g

Sources & evidence

ORD record
ord-aead37b5400348adbe03bf59dd140057
Source dataset
uspto-grants-1985_10
Patent number
US04547499

Reaction notes

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