Hydrochloric Acid → 6-Cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole
Reaktionsgleichung
C([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([C:18]#[N:19])=[C:13]3[CH2:20][CH:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:22][CH:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.C([Li])CCC.Cl>C1COCC1.CCCCCC>[C:18]([C:14]1[CH:15]=[CH:16][C:17]2[NH:9][CH2:10][CH:11]3[CH2:22][CH:21]([N:23]([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH2:20][C:13]=1[C:12]=23)#[N:19]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a stirred solution of 4.8 g (0.0124 mol) of (+)-1-benzoyl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 mL of THF cooled to -78° C. under a N2 atmosphere were added 16 mL (0.025 mol) of a 1.6 M solution of n-butyl lithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes and then allowed to warm to -20° C. To the reaction mixture was added 100 mL of 1N HCl. The mixture was extracted once with ethyl ether. The acidic solution was made alkaline with the addition of cold 5N NaOH. The basic mixture was extracted twice with CH2Cl2. The combined organic solution was washed with a saturated NaCl solution. The CH2Cl2 solution was dried over MgSO4 and evaporated to give 4 g of an oil. Chromatography of this oil over silica gel with ethyl acetate as eluent gave 3 g (85%) of product as an oil which upon standing solidified.
Aufarbeitung
- temperatureto warm to -20° C
- extractionThe mixture was extracted once with ethyl ether
- additionwith the addition of cold 5N NaOH
- extractionThe basic mixture was extracted twice with CH2Cl2
- washThe combined organic solution was washed with a saturated NaCl solution
- dry with materialThe CH2Cl2 solution was dried over MgSO4
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-2e91ec2d79624b3c8b2c24b06b897f36
- Quelldatensatz
- uspto-grants-1997_01
- Patentnummer
- US05594019
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