(4-chlorophenyl)-phenylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The racemic 4-chlorobenzhydrylamine was treated with D-tartaric acid, and then sequentially recrystallized ten times from water (as described by Clemo, et al., J. Chem. Soc., (1939), 1958-1960) to provide (S)-4-chlorobenzhydrylamine of high optical purity (ee>98%, according to chiral HPLC). sequentially recrystallized ten times from water (as described by Clemo, et al., J. Chem. Soc., (1939), 1958-1960)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following a procedure similar to that described in Example 3(b), but using S-2-pyridyl 3-cyanoandrosta-3,5-diene-17β-thiocarboxylate [prepared as described in Example 3(a)] and 4-chlorobenzhydrylamine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 70%.

Conditions: temp:-35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 80 ml of carbon disulfide and 39.82 g (0.193 mole) of dicyclohexylcarbodimide in 100 ml of anhydrous ether, under dry N2, is cooled with stirring to -35° C. Then 42.23 g (0.194 mole) of p-chlorobenzhydrylamine in 500 ml of dry ether is added over about 5 min such that the temperature within the reaction vessel does not rise above -20° C. The temperature is allowed to rise slowly over 3 hrs. to ca.25° C and stirring is continued overnight. Dicyclohexylthiourea was removed by filtration and the filtrate is taken to dryness in vacuo. The cloudy oil is treated with 500 ml of pentane which dissolves the product and precipitates more insoluble impurities. Filtration through filter aid (diatomaceous earth) and solvent removal in vacuo gives p-chlorobenzhydryl isothiocyanate as an oil; IR (neat) 2140 cm-1. under dry N2, is cooled does not rise above -20° C 25° C and stirring is continued overnight Dicyclohexylthiourea was removed by filtration The cloudy oil is treated with 500 ml of pentane which dissolves the product precipitates more insoluble impurities Filtration through filter aid (diatomaceous earth) and solvent removal in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.37 g of α-(p-chlorophenyl)benzylamine and 4.54 g of 2-methylmercapto-2-imidazoline-hydroiodide was heated at 150°-160° C. for 20 minutes. After cooling, the reaction mixture was dissolved in methanol and the solution rendered basic with sodium hydroxide to give 2-(α-(p-chlorophenyl)benzyl)iminoimidazolidine having a melting point of 187°-189° C. was heated at 150°-160° C. for 20 minutes After cooling

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following a procedure similar to that described in Example 3(b), but using S-2-pyridyl 3-cyanoandrosta-3,5-diene-17β-thiocarboxylate [prepared as described in Example 3(a)] and 4-chlorobenzhydrylamine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 70%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following a procedure similar to that described in Example 3(b), but using S-2-pyridyl 3-cyanoandrosta-3,5 -diene-17β-thiocarboxylate [prepared as described in Example 3(a)] and 4-chlorobenzhydrylamine as starting materials, in relative proportions similar to those used in that Example, the title compound was obtained in a yield of 70%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: By the procedure of Example 1, only substituting respectively for 4-chlorobenzhydrylamine and O-methylcaprolactim, appropriate amounts of 4-fluorobenzhydrylamine and O-methylvalerolactim the title compound was obtained, m.p. 211°-213°C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in a yield of 80% in a similar manner to that described in Example 2 by reacting 4-methyl-3-oxo-4-azaandrost-5-ene-17β-carboxylic acid (prepared as described in Preparation 5) and α-(4-chlorophenyl)benzylamine.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in a yield of 78% in a similar manner to that described in Example 2 by reacting 3-oxo-4-azaandrost-5-ene-17β-carboxylic acid and α-(4-chlorophenyl)benzylamine.