Acetone → HCID 23179855, compound

HRID 2227999Notes

Reaction equation

HRID 2227999 reaction equation
CC([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=O.C=O.[ClH:13].[CH3:14][NH:15][CH3:16].[CH3:17][C:18]([CH3:20])=[O:19]>C(O)C>[ClH:13].[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:17][C:18](=[O:19])[CH2:20][N:15]([CH3:16])[CH3:14])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 98284'-FluoroacetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 23179855HCID 23179855, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-fluoroacetophenone (8.8 ml, 72.4 mmol), paraformaldehyde (2.9 g, 94.1 mmol), dimethylamine hydrochloride (7.8 g, 96.78 mmol) conc. HCl (1 ml) in ethanol (10 ml) was heated under reflux for 3 hrs. The solution was added to acetone (50 ml), allowed to cool and placed in the fridge overnight. The resulting white solid was filtered washed with acetone (100 ml) and dried over P2O5 under vacuum to give 1-(4-fluorophenyl)-3-(N,N-dimethylamino)propanone hydrochloride 7.82 g, (51%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. temperatureto cool
  4. customplaced in the fridge overnight
  5. filtrationThe resulting white solid was filtered
  6. washwashed with acetone (100 ml)
  7. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-dd145dd5ca784150811796084c70751a
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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