Hydrochloric Acid → HCID 10564937, compound
Reaction equation
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][C@@H:11]3[CH2:22][C@H: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]Participants
Conditions
- Temperature
- -78 °C
Procedure
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 prepared as in Part A hereof in 200 mL of THF cooled to -78° C. under N2 atmosphere, were added 16 mL (0.025 mol) of 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 1 N HCl. The mixture was extracted once with ethyl ether. The acidic solution was made alkaline with the addition of cold 5 N NaOH. The basic mixture was extracted twice with CH2Cl2. The combined organic solution was washed with saturated aqueous 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.
Workup
- temperatureto warm to -20° C
- extractionThe mixture was extracted once with ethyl ether
- additionwith the addition of cold 5 N NaOH
- extractionThe basic mixture was extracted twice with CH2Cl2
- washThe combined organic solution was washed with saturated aqueous NaCl solution
- dry with materialThe CH2Cl2 solution was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-0fd66bf0c9434bc6a78d2f79e4f94689
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292766
Reaction notes
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