Hydrochloric Acid → N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride

HRID 410150Notes

Reaction equation

HRID 410150 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([C@H:17]([NH2:19])[CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.[Cl:20][CH2:21][CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.Cl>C(#N)C.C1(C)C=CC=CC=1.O>[ClH:20].[C:7]1([C@H:17]([NH:19][CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)[CH3:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 534418431-(3-Chloroprop-1-enyl)-3-(trifluoromethyl)benzene

Product 1

HCID 67057068N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

Anhydrous potassium carbonate (64.0 g) and (R)-1-(1-naphthyl)ethylamine (39.0 g) was added to a solution of 1-[3-chloroprop-1-en-1-yl]-3-(trifluoromethyl)benzene (Example 6; 50 g) in acetonitrile (500 mL) at room temperature. The reaction mixture was refluxed for 12 hours at 80° C. to 85° C. After completion of the reaction, the mixture was quenched with de-ionized water (250 mL). The organic layer was separated and completely distilled off to remove acetonitrile to obtain oil. The oil obtained was dissolved in toluene (500 mL) and added to de-ionized water (250 mL). The pH of this mixture was adjusted to 0.1-0.5 by adding solution of hydrochloric acid (6 N; 100 mL). The mixture was stirred at 50° C. to 60° C. for 15-20 minutes, followed by the layer separation. The organic layer was acidified with hydrochloric acid (6N; 50 mL) and stirred at 50° C. to 60° C. for 15-20 minutes. The organic layer was completely distilled off to obtain N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride.

Workup

  1. temperatureThe reaction mixture was refluxed for 12 hours at 80° C. to 85° C
  2. customAfter completion of the reaction
  3. customthe mixture was quenched with de-ionized water (250 mL)
  4. customThe organic layer was separated
  5. distillationcompletely distilled off
  6. customto remove acetonitrile
  7. customto obtain oil
  8. customThe oil obtained
  9. customfollowed by the layer separation
  10. stirringstirred at 50° C. to 60° C. for 15-20 minutes
  11. distillationThe organic layer was completely distilled off

Sources & evidence

ORD record
ord-ea70b75d8f394ddebca33f0f378b931d
Source dataset
uspto-grants-2014_06
Patent number
US08759586B2

Reaction notes

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