Hydrochloric Acid → 1-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)

HRID 1457737Notes

Reaction equation

HRID 1457737 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:10]=O.[ClH:12].[CH3:13][NH:14][CH3:15].Cl>C(O)C.CC(C)=O>[ClH:12].[CH3:13][N:14]([CH3:10])[CH2:15][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7410AcetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Acetophenone (29.1 mL, 0.25 mol), para-formaldehyde (12.0 g, 0.40 mol) and dimethyl amine hydrochloride (28.5 g, 0.35 mol) are suspended in ethanol (50 mL). Concentrated hydrochloric acid (0.5 mL) is added and the mixture is heated to reflux for 4 hours. Then acetone (200 mL) is added and the resulting clear solution is allowed to cool to ambient temperature. The precipitate is collected by filtration and crystallized from ethanol yielding the title compound (40.7 g, 76.0% of theoretical yield) as colorless crystals with mp. 158° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 4 hours
  3. filtrationThe precipitate is collected by filtration
  4. customcrystallized from ethanol yielding the title compound (40.7 g, 76.0% of theoretical yield) as colorless crystals with mp. 158° C.

Sources & evidence

ORD record
ord-117f4e2c1eb846f69b4273fe0f9b8756
Source dataset
uspto-grants-1998_12
Patent number
US05849758

Reaction notes

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