Hydrochloric Acid → 3-(Dimethylamino)-4′-methylpropiophenone hydrochloride (1:1)

HRID 1413435Notes

Reaction equation

HRID 1413435 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[ClH:11].[CH3:12][NH:13][CH3:14].[CH2:15]=O.Cl>CC(C)=O.C(O)C>[ClH:11].[CH3:12][N:13]([CH3:15])[CH2:14][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8500p-METHYLACETOPHENONEHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 124144363-(Dimethylamino)-4′-methylpropiophenone hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

53.6 Grams (g) (0.4 mole) of p-methylacetophenone, 42.4 g (0.52 mole) dimethylamine hydrochloride, 15.6 g (0.52 mole) paraformaldehyde and 64 milliliters (ml) ethanol were placed in a round-bottom flask equipped with a condenser and the mixture was heated to reflux with stirring. Next, 0.8 ml of concentrated hydrochloric acid was added to the mixture and refluxing was continued for 4 hours. The mixture was cooled and 600 ml of acetone was added. The desired product precipitated and was filtered and dried. m.p. 162°-163°. Yield: 70 g (76.9%).

Workup

  1. customequipped with a condenser
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. temperaturerefluxing
  5. temperatureThe mixture was cooled
  6. customThe desired product precipitated
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-d72a5c3798834e9180f2f37e9a19056b
Source dataset
uspto-grants-1981_02
Patent number
US04250185

Reaction notes

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