Sodium Iodide → HCID 19786585, compound

HRID 1196584Notes

Reaction equation

HRID 1196584 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.C(N(C(C)C)CC)(C)C.[O:30]=[C:31]1[N:35]([CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[C:34]2[CH:42]=[CH:43][CH:44]=[CH:45][C:33]=2[NH:32]1.[I-].[Na+]>C(OCC)(=O)C.O.CN(C=O)C>[O:30]=[C:31]1[N:35]([CH:36]2[CH2:37][CH2:38][N:39]([CH2:2][CH2:3][CH2:4][CH:5]3[C:19](=[O:20])[C:9]4[C:10]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)=[N:11][O:12][C:8]=4[CH2:7][CH2:6]3)[CH2:40][CH2:41]2)[C:34]2[CH:42]=[CH:43][CH:44]=[CH:45][C:33]=2[NH:32]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 19786584HCID 19786584, compound

Product 1

HCID 19786585HCID 19786585, compoundYield 27.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

To a solution consisting of 5-(3-chloropropyl)-6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one (4.19 g) and DMF (150 ml) was added diisopropylethyl amine (6.31 ml), 4-(2-keto-1-benzimidazolinyl)piperidine (3.46 g) and sodium iodide (2.17 g) at room temperature with stirring. The reaction was heated at 78° C. under nitrogen atmosphere with stirring (11 hours). Upon cooling to room temperature, water and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous layer extracted three times with ethyl acetate and once with ether. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude product. Purification via flash chromatography (silica gel, 1% methanol/2% Et3N/ether) afforded 1.90 g of 6,7-dihydro-5-[3-(4-(2-keto-1-benzimidazolinyl)-1-piperidinyl)-propyl]-3-phenyl-1,2-benzisoxazol-4(5H)-one, m.p. 212°-218° C.

Workup

  1. stirringwith stirring (11 hours)
  2. temperatureUpon cooling to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and concentration
  8. customgave the crude product
  9. customPurification via flash chromatography (silica gel, 1% methanol/2% Et3N/ether)

Sources & evidence

ORD record
ord-730c6009cc5a403495e11d598c95c582
Source dataset
uspto-grants-1992_05
Patent number
US05114936

Reaction notes

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