4-pentylbenzaldehyde

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: To a solution of 4-pentylbenzaldehyde (25 g, 142 mmol) and ethyl diethylphosphonoacetate (30 ml, 150 mmol) in THF was added sodium hydride (60%, 6 g, 150 mmol), and the mixture was stirred at room temperature for 12 hours and poured into ice water. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure to give the object compound as an oily substance. 39.6 g, (yield 100%) The reaction mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate anhydride the solvent was removed under reduced pressure to give the object compound as an oily substance

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

Procedure: To a solution of 4-pentylbenzaldehyde (25 g, 142 mmol) and ethyl diethylphosphonoacetate (30 ml, 150 mmol) in THF was added sodium hydride (60%, 6 g, 150 mmol), and the mixture was stirred at room temperature for 12 hours and poured into ice water. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure to give the object compound as an oily substance. 39.6 g, (yield 100%) The reaction mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate anhydride the solvent was removed under reduced pressure to give the object compound as an oily substance

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

Procedure: This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3H), 1.28 (m, 6H), 1.82 (m, 2H), 1.37 (m, 4H), 2.57 (t, 2H), 5.55+6.10 (m, 1H), 6.38 (m, 1H), 7.10 (m, 4H), 10.50 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65. Kugelrohr distillation (bp 147-151° C./0.05 torr)

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

Procedure: This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147°-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3H), 1.28 (m, 6H), 1.82 (m, 2H), 1.37 (m, 4H), 2.57 (t, 2H), 5.55+6.10 (m, 1H), 6.38 (m, 1H), 7.10 (m, 4H), 10.50 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65. Kugelrohr distillation (bp 147°-151° C./0.05 torr)

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

Procedure: This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147°-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3H), 1.28 (m, 6H), 1.82 (m, 2H), 1.37 (m, 4H), 2.57 (t, 2H), 5.55+6.10 (m, 1H), 6.38 (m, 1H), 7.10 (m, 4H), 10.50 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65. Kugelrohr distillation (bp 147°-151° C./0.05 torr)

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

Procedure: The compound was synthesized as in Example 3.1 using 4-bromobenzaldehyde (250 mg, 1.35 mmol) in place of 5-bromo-2-formylfuran and pentylboronic acid (259 mg, 2.23 mmol) in place of hexylboronic acid to give 4-pentylbenzaldehyde (161 mg, 68%). Used without further characterization.

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

Procedure: This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3 H), 1.28 (m, 6 H), 1.82 (m, 2 H), 1.37 (m, 4 H), 2.57 (t, 2 H), 5.55+6.10 (m, 1 H), 6.38 (m, 1 H), 7.10 (m, 4 H), 10.50 (bs, 1 H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65. Kugelrohr distillation (bp 147-151° C./0.05 torr)

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

Procedure: This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3H), 1.28 (m, 6H), 1.82 (m, 2H), 1.37 (m, 4H), 2.57 (t, 2H), 5.55+6.10 (m, 1H), 6.38 (m, 1H), 7.10 (m, 4H), 10.50 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65. Kugelrohr distillation (bp 147-151° C./0.05 torr)

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

Procedure: N—[(S)-1-Benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide hydrochloride (2 g, 5.55 mmol) was dissolved in methanol (50 mL), followed by the addition of triethylamine (0.562 g, 5.55 mmol) and 4-n-pentylbenzaldehyde (1.076 g, 6.10 mmol). The mixture was heated to reflux for 5 h, cooled to rt and sodium borohydride (0.6 g, 15.8 mmol) was added in several portions over a period of 60 min. Stirring at rt was continued for 12 h, followed by the addition of water (2 mL). The mixture was concentrated under reduced pressure, to the residue was added water (100 mL) and the product was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (silicagel, heptane/EtOAc=1/1) to give 906 mg (32%) of 1-(4-benzyl-piperazin-1-yl)-(S)-2-(4-pentyl-benzylamino)-3-phenyl-propan-1-one. LC-MS: tR=0.77 min; [M+H]+=484.44. The mixture was heated to reflux for 5 h The mixture was concentrated under reduced pressure, to the residue was added water (100 mL) the product was extracted with EtOAc (3×100 mL) The combined organic layers were washed with brine (100 mL) dried over magnesium sulfate filtered concentrated under reduced pressure The crude material was purified by column chromatography (silicagel, heptane/EtOAc=1/1)

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