Potassium Iodide → HCID 23287876, compound

HRID 612416Notes

Reaction equation

HRID 612416 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:24][CH2:25][CH:26]=[C:27]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[CH2:31][CH2:30][C:29]2[CH:38]=[CH:39][CH:40]=[CH:41][C:28]1=2>C(C(C)=O)C.C(OCC)(=O)C>[CH:38]1[C:29]2[CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:27](=[CH:26][CH2:25][CH2:24][N:4]3[CH2:5][CH2:6][N:1]([C:7]4[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=4[C:9]#[N:10])[CH2:2][CH2:3]3)[C:28]=2[CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 17126855-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 2735875N-(2-Cyanophenyl)piperazine

Product 1

HCID 23287876HCID 23287876, compound

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The above benzonitrile (4.89 g, 26 mmol) was dissolved in methyl ethyl ketone (100 ml), and potassium carbonate (21.7 g, 157 mmol), potassium iodide (3.45 g, 52 mmol), and 5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (8.18 g, 26 mmol), were added. The resulting mixture was stirred at reflux temperature for 18 h. After cooling to room temperature, ethyl acetate (200 ml) was added and the mixture was washed with water (2×150 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting first with a mixture of ethyl acetate and heptane (1:4), and then with a mixture of ethyl acetate and heptane (1:2). This afforded 5.60 g of the title compound as a solid.

Workup

  1. temperatureat reflux temperature for 18 h
  2. washthe mixture was washed with water (2×150 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting first with a mixture of ethyl acetate and heptane (1:4)
  6. additionwith a mixture of ethyl acetate and heptane (1:2)

Sources & evidence

ORD record
ord-1b4d6c9252d44cfd8b551fb1ad3d8b80
Source dataset
uspto-grants-1999_12
Patent number
US06004961

Reaction notes

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