Hydrochloric Acid → 1-(4-Chlorophenyl)-3-(dimethylamino)propan-1-one

HRID 399887

Reaction equation

HRID 399887 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:15])[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:5][CH:4]=1.CC(C1C=CC(Cl)=CC=1)=O.Cl.CNC.C=O.Cl>C(O)C.CC(C)=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:15])[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7467P-ChloroacetophenoneHCID 10473Dimethylamine, hydrochlorideHCID 2003701-Propanone, 1-(4-chlorophenyl)-3-(dimethylamino)-, hydrochloride (1:1)

Product 1

HCID 2003711-(4-Chlorophenyl)-3-(dimethylamino)propan-1-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

4'-Chloro-3-dimethylaminopropiophenone is prepared by treating 4'-chloro-3-dimethylaminopropiophenone hydrochloride with aqueous base to remove the HCl. The free amine is extracted into diethyl ether and recovered by evaporation of the solvent. The hydrochloride salt is prepared by the method of Maxwell in Org. Synth. Coll. Vol. III, 305-306. Thus, a mixture of 4-chloroacetophenone, dimethylamine hydrochloride, and paraformaldehyde is refluxed for 2-4 hours in 95% ethanol with a small amount of added hydrochloric acid. The solid product is obtained after adding acetone and cooling overnight.

Workup

  1. customto remove the HCl
  2. extractionThe free amine is extracted into diethyl ether
  3. customrecovered by evaporation of the solvent
  4. customThe solid product is obtained
  5. temperaturecooling overnight

Sources & evidence

ORD record
ord-3c30c644c8ca46be9c860204a7b6da4b
Source dataset
uspto-grants-1998_10
Patent number
US05824744

Linked notes

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