Isopropyl iodide → HCID 68910415, compound

HRID 1357046Notes

Reaction equation

HRID 1357046 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([C:22]([NH2:24])=[O:23])=[CH:17][CH:16]=4)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[K+].I[CH:30]([CH3:32])[CH3:31]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([C:13]3[N:14]([CH:30]([CH3:32])[CH3:31])[C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([C:22]([NH2:24])=[O:23])=[CH:17][CH:16]=4)[CH2:11][CH2:12]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 14797Potassium HydroxideHCID 53947089HCID 53947089, compound

Product 1

HCID 68910415HCID 68910415, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-(4-Chlorobenzyl)piperazinyl-indole-5-carboxamide (420 mg, 1.32 mMol) was taken in acetone. Solid KOH (280 mg, 5 mMol) was added followed by the addition of 2-iodopropane (1 g, 6 mMol) and the mixture was refluxed with stirring for 20 h. Acetone was removed in vacuo and the residue was extracted from water using methylene chloride. The extract was dried and evaporated and the residue was chromatographed on a column of silica gel using ethylacetate-hexane (ethylacetate 0 to 25%, gradient) and recrystallized from ether-hexane to yield 300 mg of the product. 1HNMR (CDCl3): δ=7.6 (s, 1H); 7.3-7.1 (m, 6H); 6.5 (s, 1H); 4.65-4.55 (m, 1H); 3.8-3.5 (m, 4H); 3.4 (s, 2H); 2.4-2.5 (s, 4H); 1.5 (d, 6H). MS (ESI) m/e 395 (M+).

Workup

  1. temperaturethe mixture was refluxed
  2. customAcetone was removed in vacuo
  3. extractionthe residue was extracted from water
  4. customThe extract was dried
  5. customevaporated
  6. customthe residue was chromatographed on a column of silica gel
  7. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-ad3e4bc8bfe34dd28fd3bf01786d8d0b
Source dataset
uspto-grants-2003_07
Patent number
US06589954B1

Reaction notes

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