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Hydrochloric Acid → 3-(Dimethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one hydrochloride

HRID 1915198
Notes
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Reaction equation

HRID 1915198 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:3].[ClH:14].[CH3:15][NH:16][CH3:17].[CH2:18]=O.Cl>C(O)C>[ClH:14].[CH3:15][N:16]([CH3:18])[CH2:17][CH2:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=1)=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 690367913-(Dimethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one hydrochlorideYield 74.8%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A mixture of 1-(3-(trifluoromethyl)phenyl)ethanone (25.0 g) (II), dimethylamine hydrochloride (13.0 g), paraformaldehyde (4.8 g), 31% w/w aqueous hydrochloric acid (0.5 mL) in ethanol (70 mL) was stirred at reflux temperature for 24 hrs, then cooled down and the solvent flushed with toluene (50 mL). The precipitated pale yellow solid was then filtrated, washed with toluene and dried to give the title compound (IV) (28.0 g).

Workup

  1. temperatureat reflux temperature for 24 hrs
  2. temperaturecooled down
  3. customthe solvent flushed with toluene (50 mL)
  4. filtrationThe precipitated pale yellow solid was then filtrated
  5. washwashed with toluene
  6. customdried

Sources & evidence

ORD record
ord-6bd2898f1ddd46e486149b630ed4be59
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08614353B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes