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

HRID 1354753ノート

反応式

HRID 1354753 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-b37722bda9c6489eba69f071cecea3a0
出典データセット
uspto-grants-2007_05
特許番号
US07223788B2

反応ノート

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