N-ethyl-N-[[(2S)-pyrrolidin-2-yl]methyl]ethanamine

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

Procedure: The title compound is prepared analogously to Example 31 from 5-(chloroacetyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and (S)-(+)-2-[(diethylamino)methyl]pyrrolidine to give a colorless highly viscous oil, [α]D20 =-10.5° (ethanol).

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

Procedure: The title compound is prepared analogously to Example 31 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (S)-(+)-2-[(diethylamino)methyl]pyrrolidine to give colorless crystals, mp. 192°-193° C. (ethyl acetate/methanol 99:1 v/v); [α]D20 =29.4° (ethanol).

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

Procedure: 110 mg of the title compound were synthesized as described for (E)-3-(4-bromophenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone, using 5-(trifluoromethyl)benzofuran-2-carboxylic acid instead of (E)-4-bromocinnamic acid and N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine instead of (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine.

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

Procedure: 110 mg of the title compound were synthesized as described for (E)-3-(4-bromophenyl)-1-((S)-2-((pyrrolidin-1-yl)methyl)pyrrolidin-1-yl)propenone, using 5-(trifluoromethyl)benzofuran-2-carboxylic acid instead of (E)-4-bromocinnamic acid and N,N-diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine instead of (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine.

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

Procedure: N,N-Diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine was synthesized as described for (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine starting with N,N-diethylamine instead of pyrrolidine.

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

Procedure: N,N-Diethyl-N-(((S)-pyrrolidin-2-yl)methyl)amine was synthesized as described for (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine starting with N,N-diethylamine instead of pyrrolidine.

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

Procedure: The title compound is prepared analogously to Example 31 from 5-(chloroacetyl)-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and (S)-(+)-2-[(diethylamino)methyl]pyrrolidine to give a colorless highly viscous oil, [α]D20 =-10.5° (ethanol).

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

Procedure: The title compound is prepared analogously to Example 31 from 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and (S)-(+)-2-[(diethylamino)methyl]pyrrolidine to give colorless crystals, mp. 192°-193° C. (ethyl acetate/methanol 99:1 v/v); [α]D20 =29.4° (ethanol).