2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)ethanamine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 1 were repeated except that 2,5-difluoronitrobenzene (1.00 g, 6.29 mmol) and 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (2.42 g, 15.7 mmol) were employed. In this case, the desired compound was obtained as a colorless liquid (2.00 g, quantitative).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 1 were repeated except that 2,5-difluoronitrobenzene (1.00 g, 6.29 mmol) and 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (2.42 g, 15.7 mmol) were employed. In this case, the desired compound was obtained as a colorless liquid (2.00 g, quantitative).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 1 were repeated except that 4-fluorobenzonitrile (1.00 g, 8.26 mmol ) and 2-(1-azabicyclo[3.3.0]octan-5-yl)ethylamine (3.15 g, 20.4 mmol) were employed. In this case, the desired compound was obtained as a colorless liquid (2.02 g, 99.1%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 1 were repeated except that 4-fluorobenzonitrile (1.00 g, 8.26 mmol ) and 2-(1-azabicyclo[3.3.0]octan-5-yl)ethylamine (3.15 g, 20.4 mmol) were employed. In this case, the desired compound was obtained as a colorless liquid (2.02 g, 99.1%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Fluorobenzonitrile (1.00 g, 8.26 mmol) and 2-(1-azabicyclo[3.3.0]octan-5-yl)ethylamine (3.15 g, 20.4 mmol) were added into anhydrous pyridine (10.0 ml) to react the mixture in a sealed tube for 10.5 hours at 180° C. After addition of water subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and refined by column chromatography to afford the desired compound (2.02 g, 95.8%), as a colorless liquid. to react the mixture in a sealed tube for 10.5 hours at 180° C to concentration in vacuo the reaction mixture was extracted by ethyl acetate dried over anhydrous sodium sulfate concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-Fluorobenzonitrile (1.00 g, 8.26 mmol) and 2-(1-azabicyclo[3.3.0]octan-5-yl)ethylamine (3.15 g, 20.4 mmol) were added into anhydrous pyridine (10.0 ml) to react the mixture in a sealed tube for 10.5 hours at 180° C. After addition of water subsequent to concentration in vacuo, the reaction mixture was extracted by ethyl acetate, dried over anhydrous sodium sulfate, concentrated in vacuo, and refined by column chromatography to afford the desired compound (2.02 g, 95.8%), as a colorless liquid. to react the mixture in a sealed tube for 10.5 hours at 180° C to concentration in vacuo the reaction mixture was extracted by ethyl acetate dried over anhydrous sodium sulfate concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 12 were repeated except that 1-chloro-4-nitrobenzene (2 04 g, 12.9 mmol) and 5-(2-aminoethyl)-1 -azabicyclo[3.3.0]octane (4.00 g, 25.9 mmol) were employed. In this case, the desired compound was obtained as a yellow liquid (2.93 g, 8 2.5%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 12 were repeated except that 1-chloro-4-nitrobenzene (2 04 g, 12.9 mmol) and 5-(2-aminoethyl)-1 -azabicyclo[3.3.0]octane (4.00 g, 25.9 mmol) were employed. In this case, the desired compound was obtained as a yellow liquid (2.93 g, 8 2.5%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 12 were repeated except that 1-chloro-2-nitrobenzene (2.04 g, 12.9 mmol) and 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (4.00 g, 25.9 mmol) were employed. In this case, the desired compound was obtained as a orange liquid (3.32 g, 98.54%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedures described in Example 12 were repeated except that 1-chloro-2-nitrobenzene (2.04 g, 12.9 mmol) and 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (4.00 g, 25.9 mmol) were employed. In this case, the desired compound was obtained as a orange liquid (3.32 g, 98.54%).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Amino-5-chloro-2-methoxybenzoic acid (1.0 g, 0.005 moles) and 1,1'-carbonyldi-imidazole (892 mg, 0.00055 moles) were suspended in the DMF (10 ml) and the mixture was stirred until solution occurred (three hours). At this time, tetrahydro-1H-pyrrolizin-7a(5H)-ethylamine [amine Heterocycles 16, 755, 1981](771 mg; 0,005 moles) was added and the mixture was stirred for 1 hour. Tlc 30% MeOH/CHCl3 /1/10% NH4OH indicated that the reaction was complete. Concentration afforded a residue which was partitioned between Et2O/H2O . The product crystallized. The solid was filtered and dissolved in CHCl3, washed with dilute K2CO3, dried over MgSO4 and concentrated to a solid. The solid was triturated with Et2O and converted to the HCl salt with MeOH/HCl to yield 1.27g (69%) of the product. (three hours) the mixture was stirred for 1 hour Concentration afforded a residue which was partitioned between Et2O/H2O The product crystallized The solid was filtered dissolved in CHCl3 washed with dilute K2CO3 dried over MgSO4 concentrated to a solid The solid was triturated with Et2O