Potassium Hydroxide → HCID 19088491, compound

HRID 1463871Notes

Reaction equation

HRID 1463871 reaction equation
[OH-:1].[K+].[C:3]([C:5]([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)[CH2:6][CH2:7][N:8]([CH3:18])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:4]>O.C(O)C>[C:19]1([C:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([CH2:6][CH2:7][N:8]([CH3:18])[CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]([NH2:4])=[O:1])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19088500HCID 19088500, compound

Product 1

HCID 19088491HCID 19088491, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A solution of potassium hydroxide (0.2 g) in water (10 ml) was added to a solution of 1-cyano-1,1-diphenyl-3-[N-methyl-N-(3-phenylprop-I-yl)amino]propane (0.22 g--see Preparation 23) in ethanol (10 ml) and the mixture was heated at 150° C. for 20 hours in a stainless steel pressure vessel then concentrated in vacuo. Water (30 ml) was added to the residue and the mixture was extracted with dichloromethane (3×30 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 viscous gum, yield, 0.11 g.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionWater (30 ml) was added to the residue
  3. extractionthe mixture was extracted with dichloromethane (3×30 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give a gum which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining methanol (0% up to 10%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c6691a7e1cb43a8ba7a72b69702e37c
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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