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

HRID 2307263Notes

Reaction equation

HRID 2307263 reaction equation
[ClH:1].O1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH2:4][CH2:3]1.Cl.[CH3:14][NH:15][CH3:16].C=O>C(O)C>[ClH:1].[CH3:14][N:15]([CH3:16])[CH2:3][CH2:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 68110Chromanone

Product 1

HCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)Yield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (0.2 ml) was dropwise added to a solution of 4-chromanone (10 g), dimethylamine hydrochloride (7.1 g) and paraformaldehyde (2.6 g) dissolved in ethanol (20 ml). The mixture was refluxed for 2 hours with heating. The mixture was allowed to cool. The resulting crystals were collected by filtration, washed with acetone and dried to obtain 9 g of β-dimethylaminopropiophenone hydrochloride (yield: 55%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturewith heating
  3. temperatureto cool
  4. filtrationThe resulting crystals were collected by filtration
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-214584f932dc49018b45606720ee7dc2
Source dataset
uspto-grants-2004_12
Patent number
US06831083B2

Reaction notes

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