Potassium Iodide → HCID 9911815, compound

HRID 1066056Notes

Reaction equation

HRID 1066056 reaction equation
[N:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:24]([C:31]1[N:32]=[C:33]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[O:34][C:35]=1[CH2:36]Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CC(C)=O>[CH2:24]([C:31]1[N:32]=[C:33]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[O:34][C:35]=1[CH2:36][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH2:6][CH2:5]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 11140808HCID 11140808, compound

Product 1

HCID 9911815HCID 9911815, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture containing 4-piperazinoindole (0.2 mmole), potassium carbonate (0.5 mmole), potassium iodide (0.08 mmole) and 4-benzyl-5-chloromethyl-2-cyclohexyl oxazole (0.19 mmole) from example 2 was stirred in acetone (2 ml) for 16 hr. The mixture was concentrated in vacuo, water (10 ml) added, and the product extracted into dichloromethane (2×10 ml). The combined organics was washed with water (5 ml), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the required product as a beige solid (94% yield). An ethanolic solution (5 ml) of the product was treated with fumaric acid (1 equivalent), and the resulting salt crystallized from diethyl ether to afford the titled product as a light beige powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo, water (10 ml)
  2. additionadded
  3. extractionthe product extracted into dichloromethane (2×10 ml)
  4. washThe combined organics was washed with water (5 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbf9c0fdb429465c91d9cde529e3dcf7
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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