Ethanol → 4-[N-(2-{2,3-dihydrobenzofur-5-yl}ethyl)-N-methylamino]-2,2-diphenylbutanamide

HRID 1587865Notes

Reaction equation

HRID 1587865 reaction equation
[C:1]([C:3]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:4][CH2:5][N:6]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][CH2:16][CH2:15][C:14]=2[CH:18]=1)[CH3:7])#[N:2].[OH-].[K+].C([OH:35])C>O>[O:17]1[C:13]2[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][N:6]([CH2:5][CH2:4][C:3]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:1]([NH2:2])=[O:35])[CH3:7])=[CH:18][C:14]=2[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 19088509HCID 19088509, compound

Product 1

HCID 190885104-[N-(2-{2,3-dihydrobenzofur-5-yl}ethyl)-N-methylamino]-2,2-diphenylbutanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture containing 1-cyano-1,1-diphenyl-3-[N-{2-(2,3-dihydrobenzofur-5-yl)ethyl}-N-methylamino]propane (0.087 g), potassium hydroxide (0.074 g), ethanol (6 ml) and water (6 ml) was heated at 140° C. in a stainless steel pressure vessel for 48 hours. On cooling to room temperature the mixture was concentrated in vacuo. Water (20 ml) was added to the residue and the mixture was extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (Na2SO4) and concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 10%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a glass, yield 0.056 g.

Workup

  1. temperatureOn cooling to room temperature the mixture
  2. concentrationwas concentrated in vacuo
  3. additionWater (20 ml) was added to the residue
  4. extractionthe mixture was extracted with dichloromethane (3×20 ml)
  5. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a gum which
  8. customwas purified by column chromatography on silica eluting with dichloromethane
  9. additioncontaining methanol (0% up to 10%)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0843f3c546c74c3a80a6215425e179fd
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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