Dimethylamine → N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

HRID 611262ノート

反応式

HRID 611262 の反応式
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[O:21][CH:22]=[CH:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:22]1[O:21][C:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C:12]3[CH:24]=[CH:25][C:9]([C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=4)=[CH:10][CH:11]=3)[CH2:16][C:17]=2[CH:23]=1)[CH3:30]

参加物

5

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196002365-[4-(4-Methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

生成物 1

HCID 19600124N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To a solution of 0.350 g (0.968 mmol) of 5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 10 ml of acetic acid, 0.131 ml (1.45 mmol) of 50% aqueous dimethylamine and 0.118 ml (1.45 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 90 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1). This was washed with diethyl ether to yield the desired product.

後処理

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (chloroform/methanol=50/1 to 25/1)
  7. washThis was washed with diethyl ether

出典と根拠

ORDレコード
ord-5e3d11b9c27149d7b5855765c307da43
出典データセット
uspto-grants-1999_12
特許番号
US05998433

反応ノート

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