Acetic Acid → N-methyl-N-benzyl(6-methyl-2-pyridyl)ethylamine

HRID 373149

Reaction equation

HRID 373149 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[N:11]=[C:10]([CH:12]=[CH2:13])[CH:9]=[CH:8][CH:7]=1.[CH3:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CO>O>[CH3:14][N:15]([CH2:13][CH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:5])[N:11]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 7669N-MethylbenzylamineHCID 707352-Ethenyl-6-methylpyridine

Product 1

HCID 14478185N-methyl-N-benzyl(6-methyl-2-pyridyl)ethylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 ml of glacial acetic acid was added to a solution of 10.0 g (84.0 mmol) of 6-methyl-2-vinylpyridine and 10.2 g (84 mmol) of N-methylbenzylamine in 100 ml of a mixture of methanol with water (1:1) and the mixture thus obtained was refluxed for 8 h. The mixture was concentrated and the residue was purified by silica gel column chromatography (chloroform/methanol/aqueous ammonia=97:3:0.3). A fraction containing the intended compound was concentrated to give the compound in the form of an oil.

Workup

  1. customthe mixture thus obtained
  2. temperaturewas refluxed for 8 h
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol/aqueous ammonia=97:3:0.3)
  5. additionA fraction containing the intended compound
  6. concentrationwas concentrated
  7. customto give the compound in the form of an oil

Sources & evidence

ORD record
ord-8b9eaeaf6a8b49d68ac7c44de1ee53df
Source dataset
uspto-grants-1992_11
Patent number
US05162347

Linked notes

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