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

HRID 1463890노트

반응식

HRID 1463890 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 120234(2-(4-Fluorophenyl)ethyl)(methyl)amineHCID 19088473HCID 19088473, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b443c62f43bd4902a1e1d99346b3012f
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05302595

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