Cesium carbonate → (R)-N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]-2-(4-phenylpiperidin-1-yl)acetamide

HRID 2426701Notes

Reaction equation

HRID 2426701 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]1([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:34][CH2:33][C@@H:32]([N:35]([CH3:37])[CH3:36])[CH2:31]2)=[CH:26][CH:25]=1)=[O:22]>C(#N)C.CN(C=O)C>[CH3:37][N:35]([CH3:36])[C@@H:32]1[CH2:33][CH2:34][N:30]([C:27]2[CH:28]=[CH:29][C:24]([NH:23][C:21](=[O:22])[CH2:20][N:16]3[CH2:15][CH2:14][CH:13]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH2:18][CH2:17]3)=[CH:25][CH:26]=2)[CH2:31]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 698734-PhenylpiperidineHCID 67147914(R)-2-chloro-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]acetamide

Product 1

HCID 58866540(R)-N-[4-(3-Dimethylaminopyrrolidin-1-yl)phenyl]-2-(4-phenylpiperidin-1-yl)acetamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Cesium carbonate (100 mg) and 4-phenylpiperidine (48 mg) were added to a solution of (R)-2-chloro-N-[4-(3-dimethylaminopyrrolidin-1-yl)phenyl]acetamide (80 mg) in acetonitrile (5 ml) and DMF (1 ml), and the mixture was kept at 65° C. for 12 hours. The mixture was freed of volatile fractions and the residue was partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography (silica gel, eluent: methanol/dichloromethane). This resulted in the product with the molecular weight of 406.58 (C25H34N4O); MS (ESI): 407 (M+H+).

Workup

  1. customthe residue was partitioned between water and dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (silica gel, eluent: methanol/dichloromethane)
  6. customThis resulted in the product with the molecular weight of 406.58 (C25H34N4O)

Sources & evidence

ORD record
ord-24917b2b366446c7bc0eee23591c8b41
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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