Potassium Carbonate → HCID 19088499, compound

HRID 1463872Notes

Reaction equation

HRID 1463872 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]([C:25]#[N:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-:30].[K+].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH2:7][N:8]([CH2:10][CH2:11][C:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:25]([NH2:26])=[O:30])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19088470HCID 19088470, compound

Product 1

HCID 19088499HCID 19088499, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3-[N-(4-chlorphenethyl)-N-methylamino]-1-cyano-1,1-diphenylpropane (0.2 g--Preparation 24) in 90% sulphuric acid (0.5 ml) was heated at 80°-85° c. for 3 hours. On cooling to room temperature, ice (10 g) was added and the mixture was basified (pH 10) by the addition of potassium carbonate. The mixture was extracted with dichloromethane (3×50 ml) and the combined dichloromethane extracts were washed with water (2×20 ml) then dried (Na2SO4) and concentrate in vacuo to give a gum. The gum was purified by column chromatography on silica eluting with hexane containing dichloromethane (25% up to 100%) followed by dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a gum, yield, 0.16 g.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  2. washthe combined dichloromethane extracts were washed with water (2×20 ml)
  3. dry with materialthen dried (Na2SO4)
  4. concentrationconcentrate in vacuo
  5. customto give a gum
  6. customThe gum was purified by column chromatography on silica eluting with hexane
  7. additioncontaining dichloromethane (25% up to 100%)
  8. additioncontaining methanol (0% up to 5%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d694f361611e46b8b5b434f9f34e1f21
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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