Hydrochloric Acid → 1-Propanone, 1-(4-chlorophenyl)-3-(dimethylamino)-, hydrochloride (1:1)

HRID 1024353

Reaction equation

HRID 1024353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][CH3:14].[CH2:15]=O.Cl>CC(C)=O.CCO>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH2:9][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7467P-ChloroacetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 2003701-Propanone, 1-(4-chlorophenyl)-3-(dimethylamino)-, hydrochloride (1:1)Yield 112%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To EtOH (80 mL), p-chloroacetophenone (77.3 g, 0.50 mol), dimethylamine hydrochloride (52.7 g, 0.65 mol), paraformaldehyde (19.8 g, 0.66 mol) and concentrated aqueous HCl (1 mL) were added and the mixture was refluxed for 5 h. The mixture was cooled to 40° C., acetone (400 mL) was added, and under stirring the mixture was cooled further to 20° C. The precipitate was filtered, washed with acetone and PA, and air dried to obtain 69.5 g of product which was used without further purification in the subsequent step.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. temperaturewas cooled further to 20° C
  3. filtrationThe precipitate was filtered
  4. washwashed with acetone and PA, and air
  5. customdried

Sources & evidence

ORD record
ord-5c99c52e2dd449b98ddccfd2181df25b
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Linked notes

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