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Hydrochloric Acid → N-Benzyl-2-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine

HRID 1284276
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1284276
[F:1][C:2]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16])([F:12])[C:3]([F:11])([F:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.C1C=CC=CC=1>[CH2:21]([NH:16][CH2:15][C:14]1[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=1[C:2]([F:12])([F:1])[C:3]([F:11])([F:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 203722482-(alpha,alpha,beta,beta-Tetrafluorophenethyl)benzylamine

Produkt 1

HCID 20372253N-Benzyl-2-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3.9 g. (0.0138 mole) of 2-(α,α,β,β -tetrafluorophenethyl)benzylamine, 1.77 g. (0.014 mole) of benzyl chloride, 2.5 g. of anhydrous potassium carbonate, and 25 ml. of benzene is stirred and heated to refluxing for about 40 hours. After filtration, the solvent is evaporated under reduced pressure, leaving the product as the residual oil. Purification is effected by column chromatography on 250 g. of silica, the product being eluted with 1% methanol in chloroform. The fractions that show one spot of rf 0.7 on a fluorescent silica thin layer plate developed with 5% methanol in chloroform are combined. Evaporation of the solvent under reduced pressure leaves the product as the residual oil. The base is converted to the hydrochloride salt by treating an ethanolic solution with a slight excess of 8N hydrogen chloride in ethanol. Dilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 188°-189.5°C. Recrystallization from acetone yields a purified sample, m.p. 188.5°-190°C.

Aufarbeitung

  1. additionA mixture of 3.9 g
  2. temperatureheated
  3. temperatureto refluxing for about 40 hours
  4. filtrationAfter filtration
  5. customthe solvent is evaporated under reduced pressure
  6. customleaving the product as the residual oil
  7. customPurification
  8. washof silica, the product being eluted with 1% methanol in chloroform
  9. customEvaporation of the solvent under reduced pressure
  10. customleaves the product as the residual oil
  11. customDilution with absolute ether precipitates the hydrochloride as white crystals, m.p. 188°-189.5°C
  12. customRecrystallization from acetone
  13. customyields a purified sample, m.p. 188.5°-190°C.

Quellen und Nachweise

ORD-Eintrag
ord-5ebb9b43ecb94f7ea505448ad0bef5e7
Quelldatensatz
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03978127

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