2-Chloropropane → 4-Amino-4-(1-(4-chlorophenyl)cyclobutyl]butan-1-ol

HRID 1650960

Reaktionsgleichung

Reaktionsgleichung von HRID 1650960
C([Mg]Cl)(C)C.[Mg].ClC(C)C.Cl[CH:12]([CH3:15])[CH2:13][OH:14].BrCC(Br)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([C:32]#[N:33])[CH2:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>O1CCCC1>[NH2:33][CH:32]([C:28]1([C:25]2[CH:24]=[CH:23][C:22]([Cl:21])=[CH:27][CH:26]=2)[CH2:29][CH2:30][CH2:31]1)[CH2:15][CH2:12][CH2:13][OH:14]

Komponenten

8

Edukt 6

HCID 63612-ChloropropaneHCID 65531,2-DibromopropaneHCID 6566Propylene ChlorohydrinHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 5462224Magnesium2×HCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 198237134-Amino-4-(1-(4-chlorophenyl)cyclobutyl]butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of isopropylmagnesium chloride [prepared by the reaction of magnesium (2.4 g) and 2-chloropropane (10 ml) in tetrahydrofuran (30 ml)] was added dropwise under argon at -20° C. to a solution of 2-chloropropan-1-ol (9.45 g) in tetrahydrofuran (100 ml). Magnesium (3.6 g) was added and the mixture was allowed to stand for twenty minutes and was then heated under relux in the presence of 1,2-dibromopropane for 40 minutes. 1-(4-Chlorophenyl)cyclobutanecarbonitrile (9 g) was added and the mixture was heated under reflux for 16 hours. The mixture was cooled and the supernatant liquid decanted from excess magnesium metal and treated with sodium borohydride (3 g) and propan-2-ol (100 ml). The mixture was heated under reflux for 5 hours. The reaction mixture was cooled, added to water and excess concentrated hydrochloric acid was added. The resulting solution was washed with toluene, basified and extracted with toluene. The extracts were dried and evaporated to give a residue which was distilled in a Buchi Kugelrohr apparatus (140°/0.4 mm) to give 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]butan-1-ol.

Aufarbeitung

  1. waitto stand for twenty minutes
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 16 hours
  4. temperatureThe mixture was cooled
  5. customthe supernatant liquid decanted from excess magnesium metal
  6. additiontreated with sodium borohydride (3 g) and propan-2-ol (100 ml)
  7. temperatureThe mixture was heated
  8. temperatureunder reflux for 5 hours
  9. temperatureThe reaction mixture was cooled
  10. additionadded to water and excess concentrated hydrochloric acid
  11. additionwas added
  12. washThe resulting solution was washed with toluene
  13. extractionextracted with toluene
  14. customThe extracts were dried
  15. customevaporated
  16. customto give a residue which
  17. distillationwas distilled in a Buchi Kugelrohr apparatus (140°/0.4 mm)

Quellen und Nachweise

ORD-Eintrag
ord-5c8801cfff244e39aedefb7b8f5b93cb
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925879

Verknüpfte Notizen

Wird geladen…