Acetonitrile → dimethyl[benzyl(methyl)amino]propanedioate

HRID 1519652Notes

Reaction equation

HRID 1519652 reaction equation
C(#N)C.[CH3:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16]>C1(C)C=CC=CC=1>[CH2:6]([N:5]([CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])[CH3:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 7669N-MethylbenzylamineHCID 70087Dimethyl bromomalonate

Product 1

HCID 222087dimethyl[benzyl(methyl)amino]propanedioateYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To an acetonitrile (60 mL) solution of N-methylbenzylamine (15 mL), an acetonitrile (10 mL) solution of dimethyl bromomalonate (12 g) was added dropwise at room temperature, and the mixture was stirred for 6 hours at room temperature. Toluene (0.20 L) was added, insolubles were filtered off, and the filtrate was concentrated under reduced pressure. To the residue, toluene (0.10 L) and OH type silica gel (6.0 g) were added, and the mixture was stirred for 20 minutes at room temperature and then filtered. The filtrate was concentrated under reduced pressure to obtain dimethyl [benzyl(methyl)amino]propanedioate (pale yellow oil) (14 g, 96%).

Workup

  1. filtrationinsolubles were filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue, toluene (0.10 L) and OH type silica gel (6.0 g) were added
  4. stirringthe mixture was stirred for 20 minutes at room temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e76fa215d20c457098063545c4562b99
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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