3-bromo-N,N-bis(trimethylsilyl)propan-1-amine

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 4.60 g of potassium phthalimide, 6.37 g of N,N-bis(trimethylsilyl)-3-bromo-1-propylamine, and 15 mL of N,N-dimethylformamide were mixed in a flask. The mixture was stirred for 6 hour while the flask was kept in an oil bath maintained at 80° C. The N,N-dimethylformamide was removed under vacuum. The residue was extracted with 90 mL of cyclohexane and filtered. The filtrate was evaporated under vacuum. The residue was triturated with 80 mL of hexane, cooled with dry ice, and then filtered to give N-[3-bis(trimethylsilyl)amino-1-propyl]phthalimide (BTMSAPPI) as a white solid (5.95 g, 76% yield). 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product: δ 7.41 (multiplet, 2H, aromatic protons), 6.85 (multiplet, 2H, aromatic protons), 3.44 (triplet, J=7.1 Hz, 2H, CH2 protons), 2.81 (multiplet, 2H, CH2 protons), 1.75 (multiplet, 2H, CH2 protons), 0.06 (singlet, 18H, Si—CH3 protons). was kept in an oil bath The N,N-dimethylformamide was removed under vacuum The residue was extracted with 90 mL of cyclohexane filtered The filtrate was evaporated under vacuum The residue was triturated with 80 mL of hexane cooled with dry ice filtered

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

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

Procedure: As shown in FIG. 9B (Scheme 4), the synthesis of 1-(3-aminopropyl)-3-benzylimidazolidin-2-one (35) will be performed by treating the starting material N1-benzylethane-1,2-diamine with diethoxymethoxyethane to form 1-benzyl-4,5-dihydro-1H-imidazole. The imidazole intermediate will be treated with BuLi (forming a lithiate) followed by quenching with water to form the final intermediate 1-benzylimidazolidin-2-one. Treating the imidazolidinone with NaH followed by Br—(CH2)3—N(SiMe3)2 under reducing conditions will afford the intermediate 35.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 4.60 g of potassium phthalimide, 6.37 g of N,N-bis(trimethylsilyl)-3-bromo-1-propylamine, and 15 mL of N,N-dimethylformamide were mixed in a flask. The mixture was stirred for 6 hour while the flask was kept in an oil bath maintained at 80° C. The N,N-dimethylformamide was removed under vacuum. The residue was extracted with 90 mL of cyclohexane and filtered. The filtrate was evaporated under vacuum. The residue was triturated with 80 mL of hexane, cooled with dry ice, and then filtered to give N-[3-bis(trimethylsilyl)amino-1-propyl]phthalimide (BTMSAPPI) as a white solid (5.95 g, 76% yield). 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product: δ 7.41 (multiplet, 2H, aromatic protons), 6.85 (multiplet, 2H, aromatic protons), 3.44 (triplet, J=7.1 Hz, 2H, CH2 protons), 2.81 (multiplet, 2H, CH2 protons), 1.75 (multiplet, 2H, CH2 protons), 0.06 (singlet, 18H, Si—CH3 protons). was kept in an oil bath The N,N-dimethylformamide was removed under vacuum The residue was extracted with 90 mL of cyclohexane filtered The filtrate was evaporated under vacuum The residue was triturated with 80 mL of hexane cooled with dry ice filtered

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 4.60 g of potassium phthalimide, 6.37 g of N,N-bis(trimethylsilyl)-3-bromo-1-propylamine, and 15 mL of N,N-dimethylformamide were mixed in a flask. The mixture was stirred for 6 hour while the flask was kept in an oil bath maintained at 80° C. The N,N-dimethylformamide was removed under vacuum. The residue was extracted with 90 mL of cyclohexane and filtered. The filtrate was evaporated under vacuum. The residue was triturated with 80 mL of hexane, cooled with dry ice, and then filtered to give N-[3-bis(trimethylsilyl)amino-1-propyl]phthalimide (BTMSAPPI) as a white solid (5.95 g, 76% yield). 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product: δ 7.41 (multiplet, 2H, aromatic protons), 6.85 (multiplet, 2H, aromatic protons), 3.44 (triplet, J=7.1 Hz, 2H, CH2 protons), 2.81 (multiplet, 2H, CH2 protons), 1.75 (multiplet, 2H, CH2 protons), 0.06 (singlet, 18H, Si—CH3 protons). was kept in an oil bath The N,N-dimethylformamide was removed under vacuum The residue was extracted with 90 mL of cyclohexane filtered The filtrate was evaporated under vacuum The residue was triturated with 80 mL of hexane cooled with dry ice filtered