Dimethylamine → 1-(2-Dimethylaminomethyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

HRID 611226ノート

反応式

HRID 611226 の反応式
[O:1]1[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.[CH3:24][NH:25][CH3:26].[CH2:27]=O>C(O)(=O)C>[CH3:24][N:25]([CH2:27][C:2]1[O:1][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:9][CH2:10][C:4]=2[CH:3]=1)[CH3:26]

参加物

5

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000531-(4,5,7,8-Tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

生成物 1

HCID 195999231-(2-Dimethylaminomethyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

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 0.230 g (0.739 mmol) of 1-(4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 80 mg (0.89 mmol) of 50% aqueous dimethylamine and 72 mg (0.89 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

後処理

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

出典と根拠

ORDレコード
ord-805b10d917324d4ea8b8c4dc7b2816a6
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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