Potassium Iodide → HCID 18538919, compound

HRID 412953Notes

Reaction equation

HRID 412953 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]([N:42]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH2:43][CH2:44]C[Cl:46])=[O:41])[CH2:36][CH2:35]1)(=[O:33])[CH3:32].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>ClCCl.C(OCC)(=O)C>[ClH:46].[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([C:40]([N:42]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH2:43][CH2:44][CH2:6][N:8]2[CH2:9][CH2:10][CH:11]([S:14][C:15]3[S:16][C:17]4[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=4[N:19]=3)[CH2:12][CH2:13]2)=[O:41])[CH2:36][CH2:35]1)(=[O:33])[CH3:32]

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 18538476HCID 18538476, compoundHCID 18539076HCID 18539076, compound

Product 1

HCID 18538919HCID 18538919, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(2-benzothiazolylthio)piperidine (505 mg, 1.44 mmol) in dry dichloromethane (4 ml) was added trifluoroacetic acid (4 ml) and stirred at room temperature for 30 min. After the solvent was removed in vacuo, the residue was dissolved in methanol (4 ml) and evaporated. The residue was dissolved in dry acetonitrile (12 ml) followed by addition of 1-acetyl-N-(3-chlorophenyl)-N-(3-chloropropyl)-4-piperidinecarboxamide (400 mg, 1.12 mmol), potassium carbonate (0.77 g, 5.6 mmol), and potassium iodide (186 mg, 1.12 mmol). After stirred at 80° C. for 8 h, the mixture was diluted with ethyl acetate (60 ml), washed with brine (60 ml), dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by preparative HPLC eluting water-acetonitrile containing 0.1% TFA. To the TFA salt was added 5% aqueous solution of potassium carbonate, extracted with ethyl acetate (30 ml), washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The residue dissolved in ethyl acetate (20 ml) was treated with 4N hydrogen chloride in ethyl acetate (0.72 ml). After the solvent was removed in vacuo, the residue was washed with ether and dried in vacuo to give the title compound (230 mg, 34%) as a white solid.

Workup

  1. customAfter the solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in methanol (4 ml)
  3. customevaporated
  4. dissolutionThe residue was dissolved in dry acetonitrile (12 ml)
  5. stirringAfter stirred at 80° C. for 8 h
  6. washwashed with brine (60 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by preparative HPLC
  10. washeluting water-acetonitrile containing 0.1% TFA
  11. additionTo the TFA salt was added 5% aqueous solution of potassium carbonate
  12. extractionextracted with ethyl acetate (30 ml)
  13. washwashed with brine
  14. dry with materialdried over anhydrous magnesium sulfate
  15. customevaporated
  16. dissolutionThe residue dissolved in ethyl acetate (20 ml)
  17. additionwas treated with 4N hydrogen chloride in ethyl acetate (0.72 ml)
  18. customAfter the solvent was removed in vacuo
  19. washthe residue was washed with ether
  20. customdried in vacuo

Sources & evidence

ORD record
ord-852569b77be34b33bae8963d439e3583
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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