Potassium Iodide → HCID 23287876, compound

HRID 367260Notes

Reaction equation

HRID 367260 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-665a7a9828474f35825a0391d445fef7
Source dataset
uspto-grants-2000_10
Patent number
US06133268

Reaction notes

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