Water → 1,3-Propanediamine, 1-[2-(trifluoromethyl)phenyl]-

HRID 2059213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059213
B.[NH2:2][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])=[CH:4][C:5]#[N:6].O>O1CCCC1.CCOCC>[F:14][C:13]([F:15])([F:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH:3]([NH2:2])[CH2:4][CH2:5][NH2:6]

Komponenten

6

Edukt 3

HCID 962WaterHCID 6331BoraneHCID 70507151beta-Amino-2-trifluoromethylcinnamonitrile

Produkt 1

HCID 130345471,3-Propanediamine, 1-[2-(trifluoromethyl)phenyl]-Ausbeute 21,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sixty (60) ml of 1 molar borane in tetrahydrofuran is added to a solution of 7.6 g of β-amino-2-trifluoromethylcinnamonitrile (prepared according to Preparation D, Part 1) in 100 ml of ether. The mixture is stirred at room temperature overnight, then treated with 10 ml of water, and stirred for 45 minutes. The resulting mixture is concentrated under reduced pressure and 200 ml of isopropanol and 80 ml of 20% hydrochloric acid are added thereto. This mixture is refluxed for 2 hours, then concentrated to a small volume. The residue is made alkaline by addition of excess of 20% sodium hydroxide and is extracted 3 times with methylene chloride. The extracts are combined, concentrated and distilled to give 1.7 g of 1-(2-trifluoromethylphenyl)-1,3-propanediamine, bp 73°-77° C./0.1 mm.

Aufarbeitung

  1. stirringstirred for 45 minutes
  2. concentrationThe resulting mixture is concentrated under reduced pressure and 200 ml of isopropanol and 80 ml of 20% hydrochloric acid
  3. additionare added
  4. temperatureThis mixture is refluxed for 2 hours
  5. concentrationconcentrated to a small volume
  6. additionby addition of excess of 20% sodium hydroxide
  7. extractionis extracted 3 times with methylene chloride
  8. concentrationconcentrated
  9. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-6f55306f23b341adb340c1fab19e3f10
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04322421

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