Reaktion #63989

Reaktionsgleichung

1-bromopropane

magnesium

1-(3-chloro-5-methylphenyl)-1-cyclobutanecarbonitrile

propyl magnesium bromide

→

1-[1-(3-chloro-5-methylphenyl)cyclobutyl]butylamine hydrochloride

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturunder reflux for two and a half hours
3. 3
   SonstigeTwo thirds of the ether was evaporated off
4. 4
   Temperaturafter cooling
5. 5
   workup.ADDITIONa solution of sodium borohydride (3.5 g) in ethanol (150 ml) added
6. 6
   workup.ADDITIONwater (50 ml) and then 5N hydrochloric acid (50 ml) added
7. 7
   SonstigeThe ether layer was separated
8. 8
   Sonstigedried
9. 9
   Sonstigeevaporated
10. 10
    Sonstigeto yield a solid which
11. 11
    Sonstigewas recrystallised from propan-2-ol

Vorschrift

A solution of 1-(3-chloro-5-methylphenyl)-1-cyclobutanecarbonitrile (8.0 g) in ether (40 ml) was added to a solution of propyl magnesium bromide [prepared by the reaction of 1-bromopropane (6.7 g) and magnesium (1.3 g)] in ether (80 ml) and the mixture heated under reflux for two and a half hours. Two thirds of the ether was evaporated off and then, after cooling, a solution of sodium borohydride (3.5 g) in ethanol (150 ml) added. The mixture was maintained at 50° C. for one hour and water (50 ml) and then 5N hydrochloric acid (50 ml) added. The ether layer was separated, dried and evaporated to yield a solid which was recrystallised from propan-2-ol to give 1-[1-(3-chloro-5-methylphenyl)cyclobutyl]butylamine hydrochloride (m.p. 145°-146° C.).

Quelle