Potassium Iodide → HCID 21327084, compound

HRID 614856Notes

Reaction equation

HRID 614856 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17]Cl)=[CH:12][C:11]=3[C:7]=2[CH:6]=1)=[O:4].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[I-].[K+]>CC(=O)CC>[OH2:4].[OH2:4].[ClH:1].[ClH:1].[N:22]1([CH2:2][C:3]([C:5]2[CH:21]=[CH:20][C:8]3[O:9][C:10]4[CH:15]=[CH:14][C:13]([C:16](=[O:19])[CH2:17][N:22]5[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]5)=[CH:12][C:11]=4[C:7]=3[CH:6]=2)=[O:4])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 12331792HCID 12331792, compound

Product 1

HCID 21327084HCID 21327084, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 19.5 g (0.06 mole) of 2,8-bis(chloroacetyl)dibenzofuran [M. Tomita, J. Pharm. Soc. Japan 56, 906-912 (1936)] 41.7 g (0.49 mole) of piperidine and 21.6 g (0.13 mole) of potassium iodide was refluxed in 200 ml of butanone for 15 minutes then maintained at room temperature for about 18 hours. The reaction mixture was diluted with 1 l. of water and extracted with ether. The ether solution was washed with several portions of water, dried over anhydrous magnesium sulfate and treated with ethereal HCl to give the desired product which was recrystallized from methanol-butanone. M.P. 306°-308° C. (dec.), λmaxH2O 254, E1cm1% 1230.

Workup

  1. additionThe reaction mixture was diluted with 1 l
  2. extractionof water and extracted with ether
  3. washThe ether solution was washed with several portions of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. additiontreated with ethereal HCl

Sources & evidence

ORD record
ord-71f710fb54db461ab698fa7f1f6fee1d
Source dataset
uspto-grants-1979_03
Patent number
US04146624

Reaction notes

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