Acetic Acid → N-(3-Phenylpropyl)-1-(3-trifluoromethylphenyl)-2-aminopropane Hydrochloride

HRID 1106947

Reaktionsgleichung

Reaktionsgleichung von HRID 1106947
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:7][CH:8]=1.[C:15]1([CH2:21][CH2:22][CH2:23][NH2:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.[BH4-].[Na+].[ClH:31]>CO>[ClH:31].[C:15]1([CH2:21][CH2:22][CH2:23][NH:24][CH:10]([CH3:11])[CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:14])([F:13])[F:1])[CH:4]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 162593-PhenylpropylamineHCID 891011-(alpha,alpha,alpha-Trifluoro-m-tolyl)acetoneHCID 4311764Sodium borohydride

Produkt 1

HCID 18790270N-(3-Phenylpropyl)-1-(3-trifluoromethylphenyl)-2-aminopropane HydrochlorideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(3-trifluoromethylphenyl)-2-propanone (102 mg, 0.50 mmol), 3-phenyl-1-propylamine (86 mg, 0.64 mmol), glacial acetic acid (8 mg, 0.13 mmol), and MeOH (2 mL) was allowed to stir at room temperature for 0.5 h. To this mixture was added over a 4-h period sodium borohydride (19 mg, 0.50 mmol) and the mixture was allowed to stir at room temperature for 20 h. The solvents were removed by warming under reduced pressure to give a small amount of an oil which was cooled and treated with 10% HCl. The crude product separated as a white solid, 122 mg (68%), mp 135-145° C. The crystals were dissolved in H2O and the solution was extracted with Et2O. The H2O portion was separated, the H2O was evaporated, and the crystals reformed; recrystallization from acetone gave 66 mg (37%) of colorless crystals, mp 167-169° C.

Aufarbeitung

  1. stirringto stir at room temperature for 20 h
  2. customThe solvents were removed
  3. temperatureby warming under reduced pressure
  4. customto give a small amount of an oil which
  5. temperaturewas cooled
  6. customThe crude product separated as a white solid, 122 mg (68%), mp 135-145° C
  7. dissolutionThe crystals were dissolved in H2O
  8. extractionthe solution was extracted with Et2O
  9. customThe H2O portion was separated
  10. customthe H2O was evaporated
  11. customrecrystallization from acetone

Quellen und Nachweise

ORD-Eintrag
ord-a7957351e1c1486ca0eebf9f5ac40e98
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057371

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