Benzyl Bromide → HCID 19088497, compound

HRID 1587869Notes

Reaction equation

HRID 1587869 reaction equation
[CH3:1][C:2]([NH:10][CH3:11])([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([N:10]([C:2]([CH3:1])([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 19088476Ethyl 3-methyl-3-(methylamino)butanoate

Product 1

HCID 19088497HCID 19088497, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing ethyl 3-methyl-3-methylaminobutanoate (95 g-see Preparation 8), benzyl bromide (72 ml), anhydrous potassium carbonate (138 g) and acetonitrile (500 ml) was heated under reflux for 1.5 hours. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane (500 ml) and 10% aqueous potassium carbonate (300 ml). The layers were separated and the aqueous layer extracted with dichloromethane (2×100 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as a mobile, colourless oil, yield 150 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane (500 ml) and 10% aqueous potassium carbonate (300 ml)
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with dichloromethane (2×100 ml)
  7. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d70a9c564fa4ebb833336de0bef430f
Source dataset
uspto-grants-1993_06
Patent number
US05219871

Reaction notes

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