1-nonylpiperazine

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: The mixture of 8,11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The compound 8-chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1). was heated at reflux for 6 h After the mixture was concentrated water (20 mL) and ethyl acetate (20 mL) were added The two phases were separated the aqueous phase was extracted with ethyl acetate (2×20 mL) The combined ethyl acetate solution was dried over magnesium sulfate filtered The filtrate was then concentrated in vacuo to dryness

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

Procedure: A mixture of 1-benzyl-4-nonylpiperazine (0.54 g, 1.80 mmol) (prepared by reacting 1-benzylpiperazine, Aldrich, with 1-bromononane, Aldrich, and NaH in DMF), palladium hydroxide on carbon (0.14 g) and cyclohexene (7 mL) in ethanol (15 mL) was heated at reflux overnight. After filtration, the filtrate was concentrated in vacuo to dryness to give 1-nonylpiperazine as an oil, 0.38 g, 100%. was heated at reflux overnight After filtration the filtrate was concentrated in vacuo to dryness

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

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

Procedure: The mixture of 8,11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The compound 8-chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1). was heated at reflux for 6 h After the mixture was concentrated water (20 mL) and ethyl acetate (20 mL) were added The two phases were separated the aqueous phase was extracted with ethyl acetate (2×20 mL) The combined ethyl acetate solution was dried over magnesium sulfate filtered The filtrate was then concentrated in vacuo to dryness

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

Procedure: A mixture of 1-benzyl-4-nonylpiperazine (0.54 g, 1.80 mmol) (prepared by reacting 1-benzylpiperazine, Aldrich, with 1-bromononane, Aldrich, and NaH in DMF), palladium hydroxide on carbon (0.14 g) and cyclohexene (7 mL) in ethanol (15 mL) was heated at reflux overnight. After filtration, the filtrate was concentrated in vacuo to dryness to give 1-nonylpiperazine as an oil, 0.38 g, 100%. was heated at reflux overnight After filtration the filtrate was concentrated in vacuo to dryness

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

Procedure: A mixture of 1-benzyl-4-nonylpiperazine (0.54 g, 1.80 mmol) (prepared by reacting 1-benzylpiperazine, Aldrich, with 1-bromononane, Aldrich, and NaH in DMF), palladium hydroxide on carbon (0.14 g) and cyclohexene (7 mL) in ethanol (15 mL) was heated at reflux overnight. After filtration, the filtrate was concentrated in vacuo to dryness to give 1-nonylpiperazine as an oil, 0.38 g, 100%. was heated at reflux overnight After filtration the filtrate was concentrated in vacuo to dryness

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

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

Procedure: The mixture of 8, 11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The title compound was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1). was heated at reflux for 6 h After the mixture was concentrated water (20 mL) and ethyl acetate (20 mL) were added The two phases were separated the aqueous phase was extracted with ethyl acetate (2×20 mL) The combined ethyl acetate solution was dried over magnesium sulfate filtered The filtrate was then concentrated in vacuo to dryness

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

Procedure: A mixture of 1-benzyl-4-nonylpiperazine (0.54 g, 1.80 mmol) (prepared by reacting 1-benzylpiperazine, Aldrich, with 1-bromononane, Aldrich, and Nail in DMF), palladium hydroxide on carbon (0.14 g) and cyclohexene (7 mL) in ethanol (15 mL) was heated at reflux overnight. After filtration, the filtrate was concentrated in vacuo to dryness to give the title compound as an oil, 0.38 g, 100%. was heated at reflux overnight After filtration the filtrate was concentrated in vacuo to dryness

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

Procedure: The mixture of 8,11-dichlorodibenz[b,f][1,4]oxazepine (0.32 g, 1.19 mmol), 1-nonylpiperazine (0.38 g, 1.79 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.72 mL, 0.73 g, 4.77 mmol) in acetonitrile (15 mL) was heated at reflux for 6 h. After the mixture was concentrated, water (20 mL) and ethyl acetate (20 mL) were added. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried over magnesium sulfate and filtered. The filtrate was then concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate/hexane (1/2) as the eluent. The compound 8-chloro-11-(4-nonyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine was obtained as a white solid (0.15 g, 28%), m.p. 64°-66° C., MS 440 (M+ +1). was heated at reflux for 6 h After the mixture was concentrated water (20 mL) and ethyl acetate (20 mL) were added The two phases were separated the aqueous phase was extracted with ethyl acetate (2×20 mL) The combined ethyl acetate solution was dried over magnesium sulfate filtered The filtrate was then concentrated in vacuo to dryness