Potassium Iodide → HCID 12340297, compound

HRID 1076905Notes

Reaction equation

HRID 1076905 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=O.[Cl:8][CH2:9][C:10]([C:12]1[CH:25]=[CH:24][C:23]2[O:22][C:21]3[C:16](=[CH:17][C:18]([C:26](=[O:29])[CH2:27]Cl)=[CH:19][CH:20]=3)[CH2:15][C:14]=2[CH:13]=1)=[O:11].[I-].[K+]>O1CCCC1>[ClH:8].[ClH:8].[N:1]1([CH2:9][C:10]([C:12]2[CH:25]=[CH:24][C:23]3[O:22][C:21]4[C:16](=[CH:17][C:18]([C:26](=[O:29])[CH2:27][N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[CH:19][CH:20]=4)[CH2:15][C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 126652-PiperidoneHCID 12340276HCID 12340276, compound

Product 1

HCID 12340297HCID 12340297, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 ml. of piperidone in 500 ml. of tetrahydrofuran were added 33.5 g (0.1 mole) of 2,7-bis(2-chloroacetyl)xanthene and 2 g of potassium iodide with warming. The reaction mixture was allowed to stand for 7 days, filtered and the filtrate evaporated to dryness, leaving a residue which was treated with dilute acid and filtered. The filtrate was made alkaline, and the resulting oily product was extracted with methylene chloride. The methylene chloride solution was acidified with ethereal HCl which gave an oily product that was recrystallized from methanol-diethyl ether then vacuum dried to give the desired product. M.P. 260°-262°C.

Workup

  1. temperaturewith warming
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. customleaving a residue which
  5. additionwas treated
  6. additionwith dilute acid
  7. filtrationfiltered
  8. extractionthe resulting oily product was extracted with methylene chloride
  9. customgave an oily product that
  10. customwas recrystallized from methanol-diethyl ether
  11. customvacuum dried

Sources & evidence

ORD record
ord-03c7c1c2b95d4be3935fc50dc2649c79
Source dataset
uspto-grants-1976_05
Patent number
US03957989

Reaction notes

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