Tetrahydrofuran → HCID 67647433, compound

HRID 400049Notes

Reaction equation

HRID 400049 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:21][CH2:22]CS([O-])(=O)=O)([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)[CH2:9]1)=[O:7].O1CCCC1.Cl.[C:41]1([C:47]2([C:53]([NH2:55])=[O:54])[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>CO.ClCCl.C(OCC)(=O)C.O>[CH3:20][C:15]1[CH:14]=[C:13]([C:10]2([CH2:21][CH2:22][N:50]3[CH2:49][CH2:48][C:47]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)([C:53]([NH2:55])=[O:54])[CH2:52][CH2:51]3)[CH2:11][CH2:12][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)[CH:18]=[CH:17][C:16]=1[CH3:19]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 30171294-Phenylpiperidine-4-carboxamide monohydrochlorideHCID 86753240HCID 86753240, compound

Product 1

HCID 67647433HCID 67647433, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent3×

Procedure

Combine 2-[1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dimethyl-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (3.0 g, 6.1 mmol) and tetrahydrofuran (45 mL)/water (15 mL). Add 4-phenyl-piperidine-4-carboxylic acid amide hydrochloride (2.2 g, 9.14 mmol) and potassium carbonate (2.6 g, 18.8 mmol). Heat to reflux. After 80 hours, evaporate the reaction mixture in vacuo to remove most of the tetrahydrofuran and then extract with dichloromethane. Separate the organic layer and extract with water. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate, 3% methanol/dichloromethane, 6% methanol/dichloromethane, and then 10% methanol/dichloromethane to give the title compound: Rf =0.44 (silica gel, 10% methanol/dichloromethane).

Workup

  1. temperatureHeat to reflux
  2. customevaporate the reaction mixture in vacuo
  3. customto remove most of the tetrahydrofuran
  4. extractionextract with dichloromethane
  5. customSeparate the organic layer
  6. extractionextract with water
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-fc57809a52ea4101928e858f11886526
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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