Réaction #4085

Équation de réaction

sulfuric acid

diisobutylaluminum hydride

2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile

potassium hydroxide

tartaric acid

→

2-[3-[(Phenylethyl)methylamino]-propyl]-2-isopropylphenylacetaldehyde

Solvants

hexane

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autrethe ether phase was separated off
2. 2
   Lavagewashed several times with sodium chloride solution
3. 3
   SéchageAfter the ether phase had been dried over sodium sulfate
4. 4
   workup.DISTILLATIONthe ether was distilled off
5. 5
   workup.DISSOLUTIONthe remaining oily residue was dissolved in 300 ml of ethyl acetate
6. 6
   workup.ADDITIONhydrochloric acid in isopropanol was added
7. 7
   workup.WAITThe mixture was left
8. 8
   workup.WAITto stand overnight
9. 9
   Filtrationafter which the precipitated hydrochloride was filtered off under suction

Mode opératoire

180 ml of a 1M solution of diisobutylaluminum hydride in hexane were added dropwise, at -5° C., to a solution of 33.4 g (0.1 mole) of 2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile in 400 ml of diethyl ether. The mixture was stirred for 1.5 hours, after which 500 ml of 10% strength sulfuric acid were added. 30 g of tartaric acid were introduced, the mixture was rendered alkaline with concentrated potassium hydroxide solution, and the ether phase was separated off and washed several times with sodium chloride solution. After the ether phase had been dried over sodium sulfate, the ether was distilled off, the remaining oily residue was dissolved in 300 ml of ethyl acetate, and hydrochloric acid in isopropanol was added. The mixture was left to stand overnight, after which the precipitated hydrochloride was filtered off under suction.

Source