Hydrochloric Acid → 4-Amino-4-(1-(4-chlorophenyl)cyclobutyl]butan-1-ol

HRID 1650961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1650961
Cl[CH2:2][CH2:3][CH2:4][OH:5].C([Mg]Cl)(C)C.[Mg].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2([C:23]#[N:24])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.[BH4-].[Na+].Cl>O1CCCC1.O.CC(O)C>[NH2:24][CH:23]([C:19]1([C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=2)[CH2:20][CH2:21][CH2:22]1)[CH2:2][CH2:3][CH2:4][OH:5]

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 123133-Chloro-1-propanolHCID 986211-(4-Chlorophenyl)cyclobutanecarbonitrileHCID 4311764Sodium borohydrideHCID 5462224MagnesiumHCID 178418918HCID 178418918, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 3-chloropropan-1-ol (95 ml) in tetrahydrofuran cooled to below -5° C. was added over 30 minutes to a solution of isopropylmagnesium chloride [prepared from magnesium (30 g), 2-chloropropane (100 ml) and tetrahydrofuran (300 ml)]. Magnesium (36 g) was added and the mixture warmed to initiate the reaction which then had to be cooled. Tetrahydrofuran (300 ml) was then added and the mixture heated under reflux for 30 minutes. 1-(4-Chlorophenyl)cyclobutanecarbonitrile (90 g) was added and the mixture heated under reflux for 16 hours and then cooled. Sodium borohydride (30 g) and then propan-2-ol (250 ml) were added and the mixture heated under reflux for 5 hours. The reaction mixture was poured into water (1 l), and acidified with excess concentrated hydrochloric acid. The resulting acidic mixture was extracted with toluene. Removal of the toluene gave a residue which was triturated with ether to give a solid which was dried, basified and extracted with ether. The ether was removed by evaportion to give a residue which was distilled (180°/1 mm to 172°/0.8 mm) to give 4-amino-4-(1-(4-chlorophenyl)cyclobutyl]butan-1-ol.

Aufarbeitung

  1. temperaturethe mixture warmed
  2. customthe reaction which
  3. temperatureto be cooled
  4. temperaturethe mixture heated
  5. temperatureunder reflux for 30 minutes
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 16 hours
  8. temperaturecooled
  9. temperaturethe mixture heated
  10. temperatureunder reflux for 5 hours
  11. extractionThe resulting acidic mixture was extracted with toluene
  12. customRemoval of the toluene
  13. customgave a residue which
  14. customwas triturated with ether
  15. customto give a solid which
  16. customwas dried
  17. extractionextracted with ether
  18. customThe ether was removed by evaportion
  19. customto give a residue which
  20. distillationwas distilled (180°/1 mm to 172°/0.8 mm)

Quellen und Nachweise

ORD-Eintrag
ord-3eadb3ab58f14c64be7f7c81d5786825
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04925879

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