Potassium Carbonate → (5-cyano-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl]-2-[N-(4-fluorophenethyl)-N-methylamino]ethane

HRID 1463890ノート

反応式

HRID 1463890 の反応式
[C:1]([C:3]1([CH2:18][CH2:19]Br)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1([CH2:18][CH2:19][N:22]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH3:21])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amineHCID 19088473HCID 19088473、化合物

生成物 1

HCID 19756476(5-cyano-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl]-2-[N-(4-fluorophenethyl)-N-methylamino]ethane

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture containing 1-[(5-cyano-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl]-2-bromoethane (3.26 g -- see Preparation 26), N-methyl-4-fluorophenethylamine (1.53 g -- see C.A. 80:P120985y), anhydrous potassium carbonate (2.76 g) and acetonitrile (50 ml) was heated under reflux for 24 hours then concentrated in vacuo. Water (50 ml) was added to the residue and the resulting mixture was extracted with dichloromethane (3×60 ml). The combined dichloromethane extracts were dried (Na2SO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 100%) and then with dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a viscous oil, yield, 1.7 g.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. concentrationthen concentrated in vacuo
  4. additionWater (50 ml) was added to the residue
  5. extractionthe resulting mixture was extracted with dichloromethane (3×60 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with hexane
  10. additioncontaining dichloromethane (25% up to 100%)
  11. additionwith dichloromethane containing methanol (0% up to 5%)
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b443c62f43bd4902a1e1d99346b3012f
出典データセット
uspto-grants-1994_04
特許番号
US05302595

反応ノート

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