Реакция #362397

Уравнение реакции

1-acetoxy-4-dibenzylamino-2-butene

dicyclohexylmethylamine

→

title compound

N,N-Dicyclohexylmethyl-N',N'-dibenzyl-2-butene-1,4-diamine

Растворители

THF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture is concentrated in vacuo to a solid which
2. 2
   workup.DISSOLUTIONis redissolved in 100 ml of THF
3. 3
   workup.ADDITIONtreated with 25 ml of 20% aqueous sodium hydroxide
4. 4
   workup.STIRRINGThe mixture is stirred for one hour
5. 5
   Концентрированиеconcentrated
6. 6
   Экстракцияextracted with diethyl ether
7. 7
   СушкаThe ether extracts are dried
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеto give a solid which
10. 10
    Другоеis then purified by crystallization from isopropanol

Методика

A solution of 1-acetoxy-4-dibenzylamino-2-butene (10.1 g, 33 mmol) and dicyclohexylmethylamine (6.8 g, 32 mmol) in 50 ml of THF is treated with tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.9 mmol) and stirred at room temperature overnight. The reaction mixture is concentrated in vacuo to a solid which is redissolved in 100 ml of THF and treated with 25 ml of 20% aqueous sodium hydroxide. The mixture is stirred for one hour, concentrated and extracted with diethyl ether. The ether extracts are dried and concentrated to give a solid which is then purified by crystallization from isopropanol. The title compound is obtained in a yield of 9.7 g (65%) as a white solid melting at 61°-62° C.

Источник