Reaction #362397

Reaction equation

1-acetoxy-4-dibenzylamino-2-butene

dicyclohexylmethylamine

→

title compound

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

Solvents

THF

Conditions

Workup

1. 1
   ConcentrationThe 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
   Concentrationconcentrated
6. 6
   Extractionextracted with diethyl ether
7. 7
   DryingThe ether extracts are dried
8. 8
   Concentrationconcentrated
9. 9
   Otherto give a solid which
10. 10
    Otheris then purified by crystallization from isopropanol

Procedure

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.

Source