Formamide → N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine

HRID 35695Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 35695
[C:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].[CH:16]([NH2:18])=[O:17]>C(O)=O>[CH:16]([NH:18][CH:1]([C:4]1([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH2:7][CH2:6][CH2:5]1)[CH3:2])=[O:17]

Komponenten

4

Edukt 2

HCID 713FormamideHCID 130831391-Acetyl-1-(3,4-dichlorophenyl)cyclobutane

Produkt 1

HCID 23292610N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

1-Acetyl-1-(3,4-dichlorophenyl)cyclobutane (9.1 g) prepared as above, formamide (6.5 ml) and 98% formic acid (3 ml) were heated at 180° C. for sixteen hours to give N-formyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine. Concentrated hydrochloric acid (20 ml) was added and the mixture heated under reflux for three hours. The solution was then cooled, washed with ether and sodium hydroxide solution added. The product was extracted with ether, and the ether extract washed with water, dried and evaporated. 1-[1-(3,4-Dichlorophenyl)cyclobutyl]ethylamine (b.p. 112°-118° at 0.2 mm Hg) was isolated by distillation. The amine was dissolved in propan-2-ol and concentrated hydrochloric acid and the solution evaporated to dryness to give 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine hydrochloride (m.p. 185°-195° C.). (Formula I R1 =Me; R2,R3 and R4 =H; R5 =4--Cl; R6 =3--Cl).

Quellen und Nachweise

ORD-Eintrag
ord-664bef448ab44b0f8c57ec63a46ed106
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767790

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