Acetonitrile → 1-Propanone, 3-(dimethylamino)-2-[(dimethylamino)methyl]-1-phenyl-

HRID 414158

Reaction equation

HRID 414158 reaction equation
[Cl-].C[CH:3]=[N+:4]=[CH:5]C.[CH3:7][N:8]([CH3:19])[CH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[C:20](#N)C>>[CH3:19][N:8]([CH3:7])[CH2:9][CH:10]([C:11](=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][N:4]([CH3:5])[CH3:20]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 770423-(Dimethylamino)-1-phenyl-1-propanoneHCID 21873455N,N-dimethylmethylene ammonium chloride

Product 1

HCID 4329041-Propanone, 3-(dimethylamino)-2-[(dimethylamino)methyl]-1-phenyl-

Procedure

The compound N,N,N',N'-tetramethyl-2-benzoyl-1,3-propanediamine (VIII) was synthesized by the method of Kinast and Tietze, Angew. Chemie. Int. Ed. 15 239-240 (1976). A mixture of 500 parts of N,N-dimethylmethylene ammonium chloride, 2600 parts of dry acetonitrile and 1035 parts of compound VII, described above, was heated to reflux under nitrogen for 15 minutes. The mixture was allowe to cool to room temperature andd then placed in the refrigerator overnight. A total of 800 parts of the hydrochloride salt of VI was isolated by filtration. The mother liquor was made basic with 10% NaOH solution and extracted with ether, the ether solution dried with anhydrous potassium carbonate and the ether evaporated under reduced pressure to yield 479 parts of a light yellow, low melting solid identified as VIII by NMR spectroscopy. The total yield of VIII was thus 93%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 15 minutes
  3. customplaced in the refrigerator overnight

Sources & evidence

ORD record
ord-b17ba8dc4b7044289d4c9e07c09834b9
Source dataset
uspto-grants-1988_12
Patent number
US04791045

Linked notes

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