Dimethylamine → (1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

HRID 614568

Reaktionsgleichung

Reaktionsgleichung von HRID 614568
C12[NH:7][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.[CH3:8][NH:9][CH3:10].[CH3:11]CO>[Pd]>[CH3:8][N:9]([CH3:11])[C@@H:10]1[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[NH2:7]

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 702EthanolHCID 5492407-Azabicyclo[4.1.0]heptane

Produkt 1

HCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A solution of the benzylamino compound is hydrogenated in two batches, each containing 30.5 g. (0.131 mole), 175 ml. EtOH, 3.4 g Pd-C and 56.5 g. (0.394 mole) of 70% HClO4, at initial pressure of 51.5 p.s.i. for 19 hours. The two reduced batches are combined, filtered through Celite, and evaporated in vacuo at 45°. The residue is cooled in ice, basified with 40% KOH to pH 11. The resulting thick suspension is extracted with ether (5 × 200 ml.), the ether extract dried (MgSO4) and evaporated through a 9" Vigreux. The residue is distilled at 13 mm to give 32.5 g. (87% yield), b.p. 77°-78.5°. ir and nmr are identical to those of the sample prepared by the reaction of 7-azabicyclo[4.1.0]heptane with dimethylamine (Procedure I, Part C).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customevaporated in vacuo at 45°
  3. temperatureThe residue is cooled in ice
  4. extractionThe resulting thick suspension is extracted with ether (5 × 200 ml.)
  5. extractionthe ether extract
  6. dry with materialdried (MgSO4)
  7. customevaporated through a 9" Vigreux
  8. distillationThe residue is distilled at 13 mm
  9. customto give 32.5 g

Quellen und Nachweise

ORD-Eintrag
ord-54680085629644229891d96f24710c80
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145435

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