Potassium Iodide → HCID 18538984, compound

HRID 1394358Notes

Reaction equation

HRID 1394358 reaction equation
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[C:27]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([N:38]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[CH:44]=2)[CH2:39][CH2:40]CCl)=[O:37])[CH2:32][CH2:31]1)(=[O:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl-].[Na+]>ClCCl.O>[F:20][C:21]([F:26])([F:25])[C:22]([OH:24])=[O:23].[C:27]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([N:38]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([Cl:49])[CH:44]=2)[CH2:39][CH2:40][CH2:6][N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][N:15]3[CH:19]=[N:18][CH:17]=[N:16]3)[CH2:12][CH2:13]2)=[O:37])[CH2:32][CH2:31]1)(=[O:29])[CH3:28]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 18538476HCID 18538476, compoundHCID 18538822HCID 18538822, compound

Product 1

HCID 18538984HCID 18538984, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-4-(1H-1,2,4-triazol-1-ylmethyl)piperidine (48 mg, 0.18 mmol) in dry dichloromethane (1.5 mL) was added trifluoroacetic acid (1.5 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled of under reduced pressure, and the residue was dissolved in methanol (1 mL). The solvent was distilled off under reduced pressure, and the residue was dissolved in dry acetonitrile (1.5 mL). To the solution were added 1-acetyl-N-(3-chlorophenyl)-N-(3-chloropropyl)-4-piperidinecarboxamide (50 mg, 0.14 mmol), potassium carbonate (77 mg, 0.56 mmol) and potassium iodide (23 mg, 0.14 mmol), and the mixture was stirred at 80° C. for 5 hours. The mixture was cooled to room temperature, and to the mixture was added water. The mixture was saturated with sodium chloride, and extracted three times with ethyl acetate (2 mL). The extracts were combined and concentrated under reduced pressure. The concentrate was purified by using HPLC to give the titled compound as a colorless oily substance (49.1 mg, 58%).

Workup

  1. distillationThe solvent was distilled of under reduced pressure
  2. dissolutionthe residue was dissolved in methanol (1 mL)
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in dry acetonitrile (1.5 mL)
  5. stirringthe mixture was stirred at 80° C. for 5 hours
  6. temperatureThe mixture was cooled to room temperature
  7. extractionextracted three times with ethyl acetate (2 mL)
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified

Sources & evidence

ORD record
ord-c115f97b82a74e60a1241f71bde1cd92
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

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