Potassium Iodide → HCID 12340297, compound

HRID 441645Notes

Reaction equation

HRID 441645 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:7][CH2:8][C:9]([C:11]1[CH:24]=[CH:23][C:22]2[O:21][C:20]3[C:15](=[CH:16][C:17]([C:25](=[O:28])[CH2:26]Cl)=[CH:18][CH:19]=3)[CH2:14][C:13]=2[CH:12]=1)=[O:10].[I-].[K+]>O1CCCC1>[ClH:7].[ClH:7].[N:1]1([CH2:8][C:9]([C:11]2[CH:24]=[CH:23][C:22]3[O:21][C:20]4[C:15](=[CH:16][C:17]([C:25](=[O:28])[CH2:26][N:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[CH:18][CH:19]=4)[CH2:14][C:13]=3[CH:12]=2)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 12340276HCID 12340276, compound

Product 1

HCID 12340297HCID 12340297, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 ml of piperidine in 500 ml of tetrahydrofuran are 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 is allowed to stand for 7 days, filtered and the filtrate evaporated to dryness, leaving a residue which is treated with dilute acid and filtered. The filtrate is made alkaline, and the resulting oily product is extracted with methylene chloride. The methylene chloride solution is acidified with ethereal HCl which gives an oily product that is recrystallized from methanol-diethyl ether then vacuum dried to give 2,7-bis(piperidinoacetyl)xanthene dihydrochloride, M.P. 260°-262° C.

Workup

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

Sources & evidence

ORD record
ord-de82cda743364bf8bfe350cfc0f94174
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

Loading…