Potassium Iodide → HCID 22287001, compound

HRID 1837619Notes

Reaction equation

HRID 1837619 reaction equation
[CH2:1]1[C@@H:9]2[C@H:4]([CH2:5][C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[CH2:8]2)[CH2:3][NH:2]1.Br[CH2:15][CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[C:19]1(=[O:28])[N:18]([CH2:17][CH2:16][CH2:15][N:2]2[CH2:3][CH:4]3[CH:9]([CH2:8][C:7]4[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=4[CH2:5]3)[CH2:1]2)[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 11084363HCID 11084363, compound

Product 1

HCID 22287001HCID 22287001, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of trans-2,3,3a,4,9,9a-hexahydro-1H-benz[f]isoindole (200 mg, 1.15 mmol), N-(3-bromopropyl)-phthalimide (309 mg, 1.15 mmol),potassium iodide (192 mg, 1.15 mmol), and potassium carbonate (320 mg, 2.31 mmol) in 10 mL of methylethyl ketone was heated at reflux for 8 hours. The mixture was cooled to room temperature, the solids were filtered, and the filtrate was concentrated in-vacuo. The residue was dry-loaded onto a 1×5 cm silica column, and eluted with ethyl acetate followed by 20% methanol/chloroform. Obtained 200 mg of an amber oil. Yield=48%. NMR (300 MHz, CDCl3) δ7.87-7.83 (m, 2H), 7.76-7.70 (m, 2H), 7.15-7.07 (m, 4H), 3.80 (t, 2H, J=7 Hz), 3.22 (m, 2H), 3.01-2.87 (m, 4H), 2.76-2.56 (m, 4H), 2.11-1.96 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. filtrationthe solids were filtered
  4. concentrationthe filtrate was concentrated in-vacuo
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-e83d4f3624d445f29fd0d8cbb929f524
Source dataset
uspto-grants-2004_08
Patent number
US06784200B2

Reaction notes

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