Potassium Carbonate → HCID 54529325, compound

HRID 1463866Notes

Reaction equation

HRID 1463866 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH2:11][CH2:12][C:13]([CH3:17])([NH:15][CH3:16])[CH3:14])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]1[O:35][C:34]2[CH:33]=[CH:32][C:28]([CH2:29][CH2:30]Br)=[CH:27][C:26]=2[O:25]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH2:11][CH2:12][C:13]([N:15]([CH2:30][CH2:29][C:28]2[CH:32]=[CH:33][C:34]3[O:35][CH2:24][O:25][C:26]=3[CH:27]=2)[CH3:16])([CH3:17])[CH3:14])[C:8]([NH2:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122072243,4-Methylenedioxyphenethyl bromideHCID 19088472HCID 19088472, compound

Product 1

HCID 54529325HCID 54529325, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 2,2-diphenyl-5-methyl-5-methylaminohexanamide (0.5 g-- see Preparation 13), 3,4-methylenedioxyphenethyl bromide (0.38 g), anhydrous potassium carbonate (0.8 g) and acetonitrile (10 ml) was heated under reflux for 5.5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml), the layers separated and the aqueous layer extracted with dichloromethane (3×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which has purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 6%). The product-containing fractions were combined and concentrated in vacuo to give an oil which solidified on standing. The solid was recrystallised from ethanol to give the title compound as colourless needles, yield 0.09 g, m.p. 165° (softens at 45°).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5.5 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous sodium carbonate (30 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (3×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customhas purified by column chromatography on silica eluting with dichloromethane
  10. additioncontaining methanol (0% up to 6%)
  11. concentrationconcentrated in vacuo
  12. customto give an oil which
  13. customThe solid was recrystallised from ethanol

Sources & evidence

ORD record
ord-bf4de708db1b46d1b11557dd077c26a6
Source dataset
uspto-grants-1994_04
Patent number
US05302595

Reaction notes

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