Water → HCID 44319341, compound

HRID 400021Notes

Reaction equation

HRID 400021 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:26][CH2:27]CS([O-])(=O)=O)[CH2:11][CH2:10][N:9]([C:12](=[O:25])[C:13]3[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=3)[CH2:8]2)[CH:2]=1.Cl.[C:34]1([C:40]2([C:46]([NH2:48])=[O:47])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1.CO.ClCCl.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:26][CH2:27][N:43]3[CH2:42][CH2:41][C:40]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)([C:46]([NH2:48])=[O:47])[CH2:45][CH2:44]3)[CH2:11][CH2:10][N:9]([C:12](=[O:25])[C:13]3[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=3)[CH2:8]2)[CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 86750922HCID 86750922, compound

Product 1

HCID 44319341HCID 44319341, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent5×

Procedure

Combine 2-[3-(pyridin-3-yl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (0.30 g, 0.65 mmol), 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (0.22 g, 0.9 mmol), and potassium carbonate (0.25 g, 1.8 mmol) in tetrahydrofuran (6 mL)/water (2 mL). Heat to reflux. After 70 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 2% methanol/dichloromethane, 4% methanol/dichloromethane, 6% methanol/dichloromethane, 8% methanol/dichloromethane, and then and 10% methanol/dichloromethane to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue

Sources & evidence

ORD record
ord-0e7aa47bb4e8488aadc41913ded3a9f7
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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