Potassium Iodide → HCID 13505767, compound

HRID 464249Notes

Reaction equation

HRID 464249 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+].[O:21]=[C:22]1[N:26]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[C:25]2[CH:33]=[CH:34][CH:35]=[CH:36][C:24]=2[NH:23]1.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[O:21]=[C:22]1[N:26]([CH:27]2[CH2:28][CH2:29][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)[CH2:31][CH2:32]2)[C:25]2[CH:33]=[CH:34][CH:35]=[CH:36][C:24]=2[NH:23]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 516892Sodium BicarbonateHCID 13505766HCID 13505766, compound

Product 1

HCID 13505767HCID 13505767, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1.33 g. (0.005 mole) of 2-(3-chloropropyl)2,4-dihydro-1H-[1,2,4]triazolo[3,4-c][1,4]benzoxazin-1-one, from Example 1, hereinabove, 0.83 g. (0.005 mole) of potassium iodide, and 2.39 g. (0.011 mole) of 4-(2-keto-1-benzimidazolinyl)piperadine in 25 ml. of DMF under a nitrogen atmosphere, was warmed to 105° C. for 4.75 hours. The solution was cooled, poured into cold sodium bicarbonate in water solution, and extracted with methylene chloride. The methylene chloride extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was chromatographed on 175 g. of silica gel and eluted with a 2% diethylamine/15% methanol/ethyl acetate, v/v/ mixture. The eluted product thus obtained was crystallized in the manner described in example 1, hereinabove, from a methylene chloride/methanol mixture to give in two crops 1.76 g., m.p. 176°-178° C. and 0.058 g., m.p. 175.5°-178° C. of the titled compound. The analytical sample had a melting point of 176.5°-177.5° C.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was chromatographed on 175 g
  7. washof silica gel and eluted with a 2% diethylamine/15% methanol/ethyl acetate, v/v/ mixture
  8. customThe eluted product thus obtained
  9. customwas crystallized in the manner
  10. customto give in two crops 1.76 g

Sources & evidence

ORD record
ord-51926dfa9bd24d41b1d68106dfa31587
Source dataset
uspto-grants-1985_10
Patent number
US04547499

Reaction notes

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