Water → 1-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

HRID 728278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728278
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[NH:20])[CH2:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>O1CCCC1>[NH2:20][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][C:14]([CH2:15][CH3:16])([OH:17])[CH2:18][CH3:19]

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 198237421-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

Produkt 1

HCID 198237701-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol (1.6 g) in dry tetrahydrofuran (20 ml) was treated under nitrogen with boranetetrahydrofuran complex (1M solution in tetrahydrofuran 10 ml) and the mixture was heated under reflux for 24 hours. The mixture was cooled in ice and water and then 2N sodium hydroxide solution were added. The resulting mixture was extracted with ether and the extracts were washed, dried and evaporated to give 1-amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol which was then converted into the corresponding dimethylamino compound by heating a mixture of the primary amine (1.5 g), 98% formic acid (4 ml) and 37-40% aqueous formaldehyde (2 ml) at 90°-95° C. for 16 hours. The reaction mixture was cooled and poured into a mixture of 16N sodium hydroxide solution (7 ml) and ice. The mixture was extracted with ether and the extract washed, dried and evaporated to give a residue which was dissolved in ether. Addition of a solution of maleic acid in ether gave 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-ethylpentan-3-ol maleate (m.p. 110°-111° C.).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe mixture was cooled in ice
  4. extractionThe resulting mixture was extracted with ether
  5. washthe extracts were washed
  6. customdried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f91dda78e00644f1ada4d4690f2d919b
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047432

Notizen zur Reaktion

Wird geladen…