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Purification by flash chromatography of the crude product using silica gel (35 g) and elution with chloroform yielded the title compound (0.85 g, 64%) as a white crystalline solid. 1 H M (CDCl3) delta=3.80 (s, 2H), 6.44 (m, 1H), 6.98 (d, J=6 Hz, 1H), 7.10-7.16 (m, 1H), 7.26 (d, J=6 Hz, 1H), 7.48 (s, 1H), 8.34 (bs, 1H).
Yield
Reaction Conditions
Operation in experiment
PREPARATION 9 1-Phenylsulfonylindole-5-acetonitrile Procedure identical to Example 1. The reagents used include the compound of Preparation 8 (0.73 g, 4.7 mmol), sodium hydride (0.25 g, 5.1 mmol), phenylsulfonyl chloride (0.6 ml, 4.7 mmol), tetrahydrofuran (50 ml). Yield: 0.55 g (40%) of the title compound as a beige solid. 1 H NMR (CDCl3) delta=3.80 (s, 2H), 6.44 (d, J=2 Hz, 1H), 7.20 (dd, J1 =2 Hz, J2 =6 Hz, 1H), 7.38-7.44 (m, 4H), 7.58 (d, J=2 Hz, 1H), 7.84 (d, J=6 Hz, 2H), 7.96 (d, J=6 Hz, 1H).
4
[ 123-75-1 ]
4-[(2-phenylethyl)amino]cyclohexanone[ No CAS ]
[ 23690-49-5 ]
[ 110-17-8 ]
[ 173906-71-3 ]
Yield
Reaction Conditions
Operation in experiment
In methanol; ethanol; hexane; ethyl acetate;
EXAMPLE 22 3-[[4-(2-Phenylethyl)amino]-1-cyclohexen-1-yl]-<strong>[23690-49-5]1H-indole-5-acetonitrile</strong> <strong>[23690-49-5]1H-indole-5-acetonitrile</strong>1 (0.25 g, 0.0016 mol), 4-[(2-phenylethyl)amino]cyclohexanone (0.522 g, 0.0024 mol) and pyrrolidine (0.5 mL) were dissolved in EtOH (80 mL) and refluxed for 24 h. A TLC (silica gel, 50% EtOAc in Hexane) showed that the reaction was not occurring, thus, the solvent volume was reduced in vacuo to a final volume of 5 mL. An additional equivalent of 4-[(2-phenylethyl)amino]cyclohexanone (0.0024 mol) and pyrrolidine (2 mL) was added. The reaction was heated at reflux for 4 h. The solvent was removed in vacuo. Silica gel chromatography (95:5:0.5 CH2 Cl2 -MeOHNH4 OH) of the residue yielded the product (0.275 g, 35%). The viscous yellow oil was dissolved in EtOAc and treated with fumaric acid in MeOH to afford the fumarate salt (0.132 g, 40%): mp 238-242 C. Anal. Calcd for C24 H25 N3.0.6 C 4 H4 O4: C 74.59; H 6.50; N 9.88. Found: C 74.66; H 6.61; N 9.80.
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