N',N'-dibenzylpropane-1,3-diamine

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: A mixture of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate (0.248 mol) and N,N-bis(phenylmethyl)-1,3-propanediamine (0.248 mol) in methanol (600 ml) was hydrogenated at 50° C. with platinum on activated carbon (5%, 5 g) as a catalyst in the presence of thiophene (4%, 5 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 109.8 g of (±)-ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate (interm. 1). the filtrate was evaporated

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

Procedure: A mixture of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate (0.248 mol) and N,N-bis(phenylmethyl)-1,3-propanediamine (0.248 mol) in methanol (600 ml) was hydrogenated at 50° C. with platinum on activated carbon (5%, 5 g) as a catalyst in the presence of thiophene (4%, 5 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 109.8 g of (±)-ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate (interm. 1). the filtrate was evaporated

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

Procedure: A mixture of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate (0.248 mol) and N,N-bis(phenylmethyl)-1,3-propanediamine (0.248 mol) in methanol (600 ml) was hydrogenated at 50° C. with platinum on activated carbon (5%, 5 g) as a catalyst in the presence of thiophene (4%, 5 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 109.8 g of (±)-ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate (interm. 1). the filtrate was evaporated

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

Procedure: Reaction under an argon flow. A mixture of 1-amino-3-dibenzylaminopropane (0.195 mol) in ethanol (225 ml) was stirred at room temperature. Ethyl propenoate (0.2 mol) was poured into the mixture and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane/CH3OH 50/45/5). The desired fractions were collected and the solvent was evaporated, yielding 27 g of N-[3-[bis(phenylmethyl)amino]propyl]-β-alanine, ethyl ester (intermediate 52). Reaction under an argon flow the reaction mixture was stirred overnight at room temperature The solvent was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/hexane/CH3OH 50/45/5) The desired fractions were collected the solvent was evaporated

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

Procedure: A mixture of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate (0.248 mol) and N,N-bis(phenylmethyl)-1,3-propanediamine (0.248 mol) in methanol (600 ml) was hydrogenated at 50° C. with platinum on activated carbon (5%, 5 g) as a catalyst in the presence of thiophene (4%, 5 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 109.8 g of (±)-ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate (interm. 1). the filtrate was evaporated