Diethyl Ether → HCID 11571995, compound

HRID 2280966Notes

Reaction equation

HRID 2280966 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:14]=[CH:13][C:10](C#N)=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].C[Mg]Br.C([O:20][CH2:21][CH3:22])C>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:6][C:7]1[CH:14]=[CH:13][C:10]([C:21](=[O:20])[CH3:22])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 247084144-[(Diethylamino)methyl]benzonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 11571995HCID 11571995, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 12.1 g of 4-[diethylaminomethyl]benzonitrile in 40 ml of toluene was added to a solution of methylmagnesium bromide (43 ml of a 3 M solution in diethyl ether) in 40 ml of toluene, and the mixture was heated to reflux. Completion of the reaction was followed by pouring into ice-water, extracting with methyl tert-butyl ether, adjusting the aqueous phase to pH 11-12 by adding NaOH, and renewed extracting with methyl tert-butyl ether. The organic phase was dried and the solvent was evaporated. 12.1 g of the title compound were obtained.

Workup

  1. temperaturethe mixture was heated to reflux
  2. extractionextracting with methyl tert-butyl ether
  3. additionby adding NaOH
  4. extractionrenewed extracting with methyl tert-butyl ether
  5. customThe organic phase was dried
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9bb96c9b3cb444638ba8a652a78fd7a0
Source dataset
uspto-grants-2015_09
Patent number
US09139557B2

Reaction notes

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