Ethyl Acetate → HCID 53934277, compound

HRID 400046Notes

Reaction equation

HRID 400046 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29]CS([O-])(=O)=O)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].I.C[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1([C:49]([NH2:51])=[O:50])[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1.[CH:52](N(CC)C(C)C)(C)C.C(OCC)(=O)C>C(#N)C.CO.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:28][CH2:29][N:46]3[CH2:45][CH2:44][C:43]([C:38]4[CH:37]=[CH:42][C:41]([CH3:52])=[CH:40][CH:39]=4)([C:49]([NH2:51])=[O:50])[CH2:48][CH2:47]3)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 867509062-[1-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethyl-methanesulfonateHCID 86753239HCID 86753239, compound

Product 1

HCID 53934277HCID 53934277, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

Combine 2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-ethyl-methanesulfonate (0.37 g, 0.7 mmol), 4-(methyl-phenyl)-piperidine-4-carboxylic acid amide hydriodide (0.7 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.07 mmol) in acetonitrile (10 mL). Heat to reflux. After 20 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate and then 10% methanol/ethyl acetate to give the title compound: Rf =0.23 (silica gel, 10% methanol/ethyl acetate).

Workup

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

Sources & evidence

ORD record
ord-206f022dffa54192ac9bc99f5c43efe8
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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