Sodium hydride → 4-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one

HRID 2102873ノート

反応式

HRID 2102873 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH2:15][CH2:14][N:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12](=[O:22])[CH:11]=1.[H-].[Na+].Br[CH:26]([CH3:41])[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])=[CH:31][CH:30]=1)=[O:28]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH2:15][CH2:14][N:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:12](=[O:22])[C:11]=1[CH:26]([CH3:41])[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])=[CH:31][CH:30]=1)=[O:28]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 442497124-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-oneHCID 442497132-Bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one

生成物 1

HCID 250296504-[(2,4-dichlorophenyl)amino]-3-{2-[4-(1-ethoxyethoxy)phenyl]-1-methyl-2-oxoethyl}-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one収率 138.9%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

4-[(2,4-dichlorophenyl)amino]-1-piperidin-1-yl-5,6-dihydropyridin-2(1H)-one (450 mg, 1.323 mmol) suspended in THF (7 ml) was added during 15 min to NaH (67 mg, 2.645 mmol) suspended in THF (5 ml) at 5° C. under nitrogen. After the resulting mixture had been stirred at 0° C. for 1 h tetrabutylammonium iodide (49 mg, 0.132 mmol) was added followed by dropwise addition of 2-bromo-1-[4-(1-ethoxyethoxy)phenyl]propan-1-one (597 mg, 1.984 mmol) dissolved in THF (5 ml) during 15 min. After the addition the cooling bath was removed and the reaction was continued at rt overnight. Water was added and the solvent was removed by evaporation. The residue was partitioned between DCM and water. The organic phase was dried (MgSO4), filtered and evaporated to yield an orange oil (1.030 g, 90%).

後処理

  1. additionwas added
  2. additionAfter the addition the cooling bath
  3. customwas removed
  4. additionWater was added
  5. customthe solvent was removed by evaporation
  6. customThe residue was partitioned between DCM and water
  7. dry with materialThe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-f19bad9e5e5e414f8ac117ac4af3749f
出典データセット
uspto-grants-2009_08
特許番号
US07576095B2

反応ノート

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