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

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.

1. temperatureIt was cooled to 10°
2. customthe temperature below 15°
3. customthe solvent was evaporated
4. temperatureheating
5. additionNaOH (500 ml. of 20% solution) was added
6. temperaturethe mixture heated at 95° for 1 hour
7. temperaturecooled
8. extractionextracted with ether (5×100 ml.)
9. extractionThe ether solution was extracted with 10% HCl (6×100 ml.)
10. extractionThe acid extract
11. temperaturewas cooled
12. extractionextracted well with ether
13. washThe ether solution was washed with H2O, saturated salt solution
14. dry with materialdried (MgSO4)
15. customevaporated
16. distillationDistillation at 0.4 mm
17. customgave 61 g

ORD-Eintrag

ord-d2a028f0ee04428898984ef4fb6b06a2

Quelldatensatz

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04197308