Triethylamine → Ethyl 4-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)butanoate

HRID 517820

Reaktionsgleichung

Reaktionsgleichung von HRID 517820
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[CH2:11]([O:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)[CH3:12].C(N(CC)CC)C.Cl.[CH3:28][N:29]1[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]1>C(O)C>[CH3:28][N:29]1[CH2:34][CH2:33][C:32]2[N:8]([CH2:17][CH2:16][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:19])[C:5]3[CH:4]=[CH:3][C:2]([CH3:10])=[CH:7][C:6]=3[C:31]=2[CH2:30]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 18474Ethyl 4-chlorobutyrateHCID 122100571-Methylpiperidin-4-one hydrochloride

Produkt 1

HCID 44159096Ethyl 4-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)butanoateAusbeute 11,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Preparation of the title compound was carried out according to General Method 1 by using p-Tolylhydrazine hydrochloride (600 mg, 3.7 mmol), ethyl-4-chlorobutyrate (0.54 ml, 3.7 mmol), triethylamine (1.5 ml, 11.3 mmol) and N-methyl-4-piperidone hydrochloride (0.563 g, 3.7 mmol) in ethanol (10 ml) to obtain 130 mg of ethyl 4-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)butanoate after purification on silica gel (230-400 mesh) chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.

Quellen und Nachweise

ORD-Eintrag
ord-b17996800eb1421faf6af1e04bf13769
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115137B2

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