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Potassium Iodide → HCID 18538872, compound

HRID 412937
Notes
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Reaction equation

HRID 412937 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[S:13][C:12]([S:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:11][N:10]=1.[C:21]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]([N:32]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[CH2:33][CH2:34][CH2:35]Cl)=[O:31])[CH2:26][CH2:25]1)(=[O:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl-].[Na+]>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:21]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]([N:32]([C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=2)[CH2:33][CH2:34][CH2:35][N:18]2[CH2:19][CH2:20][CH:15]([S:14][C:12]3[S:13][C:9]([CH3:8])=[N:10][N:11]=3)[CH2:16][CH2:17]2)=[O:31])[CH2:26][CH2:25]1)(=[O:23])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 18538456HCID 18538456, compoundHCID 18538476HCID 18538476, compound

Product 1

HCID 18538872HCID 18538872, compound

Reagents, catalysts & solvents

1
HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

4-(5-Methyl-1,3,4-thiadiazol-2-ylthio)piperidine trifluoroacetate (59 mg, 0.18 mmol) 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 saturated sodium chloride solution (3 mL). The mixture was 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 (32.2 mg, 28%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted three times with ethyl acetate (2 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe concentrate was purified

Sources & evidence

ORD record
ord-2ebd06ffe6e7402898b28e7a1016bd76
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562978B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes