Potassium Iodide → HCID 18700234, compound

HRID 355385Notes

Reaction equation

HRID 355385 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:7]1([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[O:6][CH2:5]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br.[C:24](=[O:27])([O-])[O-].[K+].[K+].[I-].[K+]>CC(CC(C)=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:7]1([CH2:8][CH2:9][N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:10]3[CH2:11][CH2:12][C:7]4([C:13]5[C:14](=[CH:15][C:2]([CH3:1])=[CH:3][CH:4]=5)[CH2:24][O:27]4)[CH2:8][CH2:9]3)[CH2:11][CH2:12]1)[O:6][CH2:5]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 10330521HCID 10330521, compound

Product 1

HCID 18700234HCID 18700234, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A solution of 5-methyl-spiro[isobenzofuran-1(3H),4'-piperidine] (4 g), 1,6-dibromo-hexane (2.2 g), finely powdered potassium carbonate (2.7 g) and a crystal of potassium iodide in MIBK (150 ml) was refluxed for 4 h. Inorganic salts were filtered off and MIBK evaporated. Column chromatography on silica gel (eluted with ethyl acetate/ethanol/triethylamine 75:25:4) gave the pure title compound 11a. Yield 1.0 g. Mp 113°-116° C. (recrystallized from 2-propyl ether). 1H NMR (CDCl3)δ1.30-1.45 (m,4 H), 1.50-1.65 (m,4 H), 1.80 (d,4 H), 2.00 (dt,4 H), 2.35 (s,6 H), 2.45-2.50 (m,8 H). 2.85 (broad d,4 H), 5.05 (s, 4 H), 6.95-7.10 (m,6H).

Workup

  1. filtrationInorganic salts were filtered off
  2. customMIBK evaporated

Sources & evidence

ORD record
ord-53ff2d888138433b8f0612d5292c3f0b
Source dataset
uspto-grants-1998_11
Patent number
US05830896

Reaction notes

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