Reaktion #54527

Reaktionsgleichung

Benzylamine

NaH

trans-2-dimethylaminocyclohexanol

methanesulfonyl chloride

→

N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine

Ausbeute 65.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturIt was cooled to 10°
2. 2
   Sonstigethe temperature below 15°
3. 3
   Sonstigethe solvent was evaporated
4. 4
   Temperaturheating
5. 5
   workup.ADDITIONNaOH (500 ml. of 20% solution) was added
6. 6
   Temperaturthe mixture heated at 95° for 1 hour
7. 7
   Temperaturcooled
8. 8
   Extraktionextracted with ether (5×100 ml.)
9. 9
   ExtraktionThe ether solution was extracted with 10% HCl (6×100 ml.)
10. 10
    ExtraktionThe acid extract
11. 11
    Temperaturwas cooled
12. 12
    Extraktionextracted well with ether
13. 13
    WaschenThe ether solution was washed with H2O, saturated salt solution
14. 14
    Trocknendried (MgSO4)
15. 15
    Sonstigeevaporated
16. 16
    workup.DISTILLATIONDistillation at 0.4 mm
17. 17
    Sonstigegave 61 g

Vorschrift

A solution of trans-2-dimethylaminocyclohexanol (58 g.; 0.405 mole) in 80 ml. of THF was added during 10 minutes to a suspension of NaH (17.05 g.; 0.405 mole of 57% dispersion in mineral oil) in 240 ml. of THF and the mixture was refluxed for 3 hours. It was cooled to 10°, and methanesulfonyl chloride (46.39 g.; 0.405 mole) was added dropwise during 30 minutes keeping the temperature below 15°. Benzylamine (86.79 g.; 0.81 mole) was then added during 5 minutes, the solvent was evaporated and heating continued at 95° for 16 hours. NaOH (500 ml. of 20% solution) was added and the mixture heated at 95° for 1 hour, cooled and extracted with ether (5×100 ml.). The ether solution was extracted with 10% HCl (6×100 ml.) and backwashed once with ether (discard). The acid extract was cooled, basified with 20% NaOH and extracted well with ether. The ether solution was washed with H2O, saturated salt solution, dried (MgSO4) and evaporated. Distillation at 0.4 mm gave 61 g. (65% yield) of N,N-dimethyl-N'-benzyl-1,2-cyclohexanediamine, b.p. 112°. It was identical by tlc to the sample prepared by the reaction of benzylamine with trans-2-chloro-dimethylaminocyclohexane.

Quelle