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

HRID 1463890Notes

Reaction equation

HRID 1463890 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b443c62f43bd4902a1e1d99346b3012f
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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