HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 1-cyano-1,1-diphenyl-3-[N-{2-(2,3-dihydrobenzofur-5-yl)ethyl}-N-methylamino]propane

HRID 1463892
Notes
Print preview

Reaction equation

HRID 1463892 reaction equation
Br[CH2:2][CH2:3][C:4]([C:17]#[N:18])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([CH2:28][CH2:29][NH:30][CH3:31])=[CH:27][C:22]=2[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]([C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][N:30]([CH2:29][CH2:28][C:26]1[CH:25]=[CH:24][C:23]2[O:19][CH2:20][CH2:21][C:22]=2[CH:27]=1)[CH3:31])#[N:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 965754-Bromo-2,2-diphenylbutyronitrileHCID 19756475HCID 19756475, compound

Product 1

HCID 190885091-cyano-1,1-diphenyl-3-[N-{2-(2,3-dihydrobenzofur-5-yl)ethyl}-N-methylamino]propane

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 3-bromo-1-cyano-1,1-diphenylpropane (0.3 g -- see Preparation 4), N-[2-(2,3-dihydrobenzofur-5-yl) ethyl]-N-methylamine (0.177 g -- see Preparation 28), anhydrous potassium carbonate (0.276 g) and acetonitrile (25 ml) was heated under reflux for 48 hours. On cooling to room temperature, the mixture was concentrated in vacuo and the residue was partitioned between water (20 ml) and dichloromethane (40 ml). The layers were separated and the aqueous layer further extracted with dichloromethane (2×20 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 (50% 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 an oil, yield, 0.13 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue was partitioned between water (20 ml) and dichloromethane (40 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer further extracted with dichloromethane (2×20 ml)
  7. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto give an oil which
  10. customwas purified by column chromatography on silica eluting with hexane
  11. additioncontaining dichloromethane (50% up to 100%)
  12. additionwith dichloromethane containing methanol (0% up to 5%)
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46e69c5776af48b1baad2a4705511154
Source dataset
uspto-grants-1994_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05302595

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes