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Potassium Iodide → 1,1-Dimethylethyl 4-(4-{[3-(2-methyl-1-piperidinyl)propyl]oxy}phenyl)-1-piperazinecarboxylate

HRID 1434588
Notes
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Reaction equation

HRID 1434588 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23]Cl)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][NH:35]1>CC(=O)CC.O>[CH3:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][N:35]1[CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[CH:15][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 79742-MethylpiperidineHCID 11430Potassium CarbonateHCID 588178434-[4-(3-Chloro-propoxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 579358121,1-Dimethylethyl 4-(4-{[3-(2-methyl-1-piperidinyl)propyl]oxy}phenyl)-1-piperazinecarboxylateYield 88.2%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

1,1-Dimethylethyl 4-{4-[(3-chloropropyl)oxy]phenyl}-1-piperazinecarboxylate (D9) (1.6 g), was dissolved in 2-butanone (10 ml). Potassium carbonate (1.38 g) and a catalytic amount of potassium iodide were added, followed by 2-methylpiperidine (0.99 g). The mixture was heated at reflux for 72 h under nitrogen. The reaction mixture was diluted with water and extracted with dichloromethane. The organic phases were separated using a hydrophobic frit, combined and evaporated in vacuo. The residue was purified on a 100 g silica SPE bond elut cartridge, eluting with a gradient of 0% to 20% [0.880 ammonia-methanol (1:9)]-dichloromethane mixtures, to give the title compound (1.66 g). LCMS RT=2.48 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 72 h under nitrogen
  3. extractionextracted with dichloromethane
  4. customThe organic phases were separated
  5. customevaporated in vacuo
  6. customThe residue was purified on a 100 g silica SPE bond elut cartridge
  7. washeluting with a gradient of 0% to 20% [0.880 ammonia-methanol (1:9)]-dichloromethane mixtures

Sources & evidence

ORD record
ord-fbb85dd625344279bfbf535f430b3292
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615550B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes