Phenethyl bromide → 8-chloro-2,3,4,5-tetrahydro-2-methyl-5-phenethyl-1H-pyrido[4,3-b]indole

HRID 509688

Reaktionsgleichung

Reaktionsgleichung von HRID 509688
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]1([CH2:17][CH2:18]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.Cl.[CH3:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1.FC(F)(F)C([O-])=O>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]([CH2:18][CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:32]3[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][C:31]=3[C:5]=2[CH:4]=1

Komponenten

7

Edukt 5

HCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 84468TrifluoroacetateHCID 122100571-Methylpiperidin-4-one hydrochloride

Produkt 1

HCID 578759368-chloro-2,3,4,5-tetrahydro-2-methyl-5-phenethyl-1H-pyrido[4,3-b]indoleAusbeute 1,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Preparation of the title compound was carried out according to General Method 8. 4-Chlorophenylhydrazine hydrochloride (500 mg, 2.79 mmol), 2-phenyl ethyl bromide (0.38 ml, 2.79 mmol), triethyl amine (0.39 ml, 2.79 mmol) and N-methyl-4-piperidone hydrochloride (623 mg, 4.18 mmol) were combined in ethanol (2 ml) to obtain 15 mg of 8-chloro-2,3,4,5-tetrahydro-2-methyl-5-phenethyl-1H-pyrido[4,3-b]indole as a trifluoroacetate salt after purification on neutral alumina using ethyl acetate-hexane gradient followed by reverse-phase chromatography (C-18, 500 mm×50 mm, Mobile Phase A=0.05% TFA in water, B=0.05% TFA in acetonitrile, Gradient: 10% B to 80% B in 30 min, injection vol. 5 mL).

Quellen und Nachweise

ORD-Eintrag
ord-5eee7a1f408b4bffaa50173b7dc3b272
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096591B2

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