Triethylamine → 3-Acryloyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 657555ノート

反応式

HRID 657555 の反応式
Cl.[CH3:2][O:3][C:4]1[C:14]([O:15][CH3:16])=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>ClCCl>[C:24]([N:10]1[CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([O:3][CH3:2])[C:14]([O:15][CH3:16])=[CH:13][C:7]=2[CH2:8][CH2:9]1)(=[O:27])[CH:25]=[CH2:26]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 220040987,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

生成物 1

HCID 685327813-Acryloyl-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

At ambient temperature, 70 g (287.2 mmol) of the product obtained in Step 2 are dissolved in 1200 mL of dichloromethane, and then 100 mL (718 mmol/2.5 eq.) of triethylamine are added all at once. The mixture is brought to 0° C. and a solution of 25.8 mL (315.9 mmol/1.1 eq.) of acryloyl chloride in 270 mL of dichloromethane is poured in dropwise, maintaining the temperature at about 0° C. After 2 hours at 0° C., the mixture is stirred at ambient temperature overnight. Washing with 750 mL of water, 750 mL of 1N hydrochloric acid and 750 mL of water and then drying over magnesium sulphate are then carried out. After filtration and evaporation, the residue is chromatographed over 3.2 kg of silica (eluant: dichloromethane/ethanol: 95/5), followed by recrystallisation from isopropanol. After filtration over a frit and drying in vacuo at 50° C., the desired product is obtained.

後処理

  1. customis brought to 0° C.
  2. washWashing with 750 mL of water, 750 mL of 1N hydrochloric acid and 750 mL of water
  3. dry with materialdrying over magnesium sulphate
  4. filtrationAfter filtration and evaporation
  5. customthe residue is chromatographed over 3.2 kg of silica (eluant: dichloromethane/ethanol: 95/5)
  6. customfollowed by recrystallisation from isopropanol
  7. filtrationAfter filtration over a frit
  8. customdrying in vacuo at 50° C.

出典と根拠

ORDレコード
ord-01fa4a3c5f0240519da7d7926605189f
出典データセット
uspto-grants-2011_12
特許番号
US08076325B2

反応ノート

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