N,N-dimethyl-3-piperazin-1-ylpropan-1-amine

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:

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

Procedure: A mixture of 4-benzyloxycarbonyl-3-dimethylaminopropylpiperazine (2.21 g, 7.2 mmol), 5% Pd/C (0.36 g) in methanol (20 ml) was stirred under hydrogen atmosphere at room temperature for 38 h. After removal of catalyst by Celite filtration, the filtrate was concentrated to afford 1.20 g (97.6%) of orange color viscous oil. After removal of catalyst by Celite filtration the filtrate was concentrated

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

Procedure: The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with 1-(3-dimethylaminopropyl)piperazine. A yellow solid 134 was obtained (0.0401 g, 73%). MS (APCI) m/z 559 (M+H)+.

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

Procedure: The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 118 (0.033 g, 0.0779 mmol) and 3-hydroxypyrrolidine with 1-(3-dimethylaminopropyl)piperazine. A yellow solid 134 was obtained (0.0401 g, 73%). MS (APCI) m/z 559 (M+H)+.

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

Procedure: The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with 1-(3-dimethylaminopropyl)piperazine. A yellow solid 113 was obtained (0.0414 g, 79%). 1H NMR (CDCl3, 400 MHz) δ 2.20-2.50 (br, 6H), 2.42-2.50 (m, 2H), 2.86 (s, 6H), 3.21-3.28 (m, 2H), 3.32-3.38 (br, 2H), 3.83 (s, 3H), 4.05-4.10 (br, 2H), 6.88 (s, 1H), 6.99-7.06 (m, 3H), 7.10 (d, J=8.2 Hz, 1H), 7.43-7.52 (m, 3H), 7.85 (s, 1H), 8.25 (d, J=5.5 Hz, 1H); MS (APCI) m/z 531 (M+H)+.

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

Procedure: The title compound was prepared according to the procedures of Example 38E, substituting compound 76 with compound 96 (0.039 g, 0.0985 mmol) and 3-hydroxypyrrolidine with 1-(3-dimethylaminopropyl)piperazine. A yellow solid 113 was obtained (0.0414 g, 79%). 1H NMR (CDCl3, 400 MHz) δ 2.20-2.50 (br, 6H), 2.42-2.50 (m, 2H), 2.86 (s, 6H), 3.21-3.28 (m, 2H), 3.32-3.38 (br, 2H), 3.83 (s, 3H), 4.05-4.10 (br, 2H), 6.88 (s, 1H), 6.99-7.06 (m, 3H), 7.10 (d, J=8.2 Hz, 1H), 7.43-7.52 (m, 3H), 7.85 (s, 1H), 8.25 (d, J=5.5 Hz, 1H); MS (APCI) m/z 531 (M+H)+.

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

Procedure: A mixture of 100 g (1.2 mole) of piperazine, 72 g (0.455 mole) of 3-chloro-N,N-dimethylpropanamine, hydrochloride and 110 g (1.3 mole) of sodium bicarbonate in 500 ml of ethanol was heated under reflux for 7 hr, allowed to cool, filtered and concentrated to dryness under vacuum. The concentrate was slurried in dichloromethane and filtered. The filterate was concentrated and then distilled under water pump pressure (~5 mm) to afford 34 g (44%) of the desired product, bp 100°-102°/5 mm. was heated under reflux for 7 hr to cool filtered concentrated to dryness under vacuum filtered The filterate was concentrated distilled under water pump pressure (~5 mm)

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

Procedure: A mixture of 100 g (1.2 mole) of piperazine, 72 g (0.455 mole) of 3-chloro-N,N-dimethylpropanamine, hydrochloride and 110 g (1.3 mole) of sodium bicarbonate in 500 ml of ethanol was heated under reflux for 7 hr, allowed to cool, filtered and concentrated to dryness under vacuum. The concentrate was slurried in dichloromethane and filtered. The filterate was concentrated and then distilled under water pump pressure (~5 mm) to afford 34 g (44%) of the desired product, bp 100°-102°/5 mm. was heated under reflux for 7 hr to cool filtered concentrated to dryness under vacuum filtered The filterate was concentrated distilled under water pump pressure (~5 mm)

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

Procedure: The title compound was prepared according to general procedure AT using ethyl 3-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,2,4-oxadiazole-5-carboxylate (30 mg, 0.08 mmol), N,N-dimethyl-3-(piperazin-1-yl)propan-1-amine (27 mg, 0.16 mmol) and trimethylaluminium (2 M in toluene, 0.08 mL) in DCE (5 mL). The crude product was purified using FCC, eluting with 95:4.5:0.5 DCM:MeOH:NH3, to afford the title compound. The title compound was prepared The crude product was purified eluting with 95:4.5:0.5 DCM