1-chlorodecane

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: 3-Hydroxypropyl decyl ether (Compound 17) To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. 1H NMR (360 MHz; CDCl3): (0.87 (3H, t, J 7 Hz, Me), 1.25 (14H, br s, 7×CH2), 1.55 (2H, quintet, J 7 Hz, (—H2), 1.82(2H, quintet, J 5.5 Hz, 2-H2), 2.62 (1H, br s, OH), 3.41 (2H, t, J 7.5 Hz, (—H2), 3.60 (2H, t, J 5.5 Hz, 1-H2), and 3.77 (2H, t, J 5.5 Hz, 3-H2); ESI-MS (m/z, +ve): 217 (MH+, 100%). extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: 3-Hydroxypropyl decyl ether (Compound 17) To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. 1H NMR (360 MHz; CDCl3): (0.87 (3 H, t, J 7 Hz, Me), 1.25 (14 H, br s, 7×CH2), 1.55 (2 H, quintet, J 7 Hz, (—H2), 1.82 (2 H, quintet, J 5.5 Hz, 2-H2), 2.62 (1 H, br s, OH), 3.41 (2 H, t, J 7.5 Hz, (—H2), 3.60 (2 H, t, J 5.5 Hz, 1-H2), and 3.77 (2 H, t, J 5.5 Hz, 3-H2); ESI-MS (m/z, +ve): 217 (MH+, 100%). extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: 3-Hydroxypropyl decyl ether (Compound 17) To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. 1H NMR (360 MHz; CDCl3): (0.87 (3 H, t, J 7 Hz, Me), 1.25 (14 H, br s, 7×CH2), 1.55 (2 H, quintet, J 7 Hz, (—H2), 1.82 (2 H, quintet, J 5.5 Hz, 2-H2), 2.62 (1 H, br s, OH), 3.41 (2 H, t, J 7.5 Hz, (—H2), 3.60 (2 H, t, J 5.5 Hz, 1-H2), and 3.77 (2 H, t, J 5.5 Hz, 3-H2); ESI-MS (m/z, +ve): 217 (MH+, 100%). extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: 3-Hydroxypropyl decyl ether (Compound 17) To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: 3-Hydroxypropyl decyl ether (Compound 17) To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

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

Procedure: To a mixture of NaH (2.6 g, 70 mmol) and anhydrous NaI (9.9 g, 70 mmol) in dry DMF (80 mL) under N2 was added dropwise a solution of 1,3-propanediol (4.75 mL, 70 mmol) in DMF (20 mL). The mixture was stirred until hydrogen evolution had ceased, decyl chloride (1.34 g, 7.6 mmol) was added and stirring was continued at 50° C. for 18 hours. Then, the reaction mixture was poured into H2O (300 mL) and extracted with diethyl ether (3×250 mL). The organic extracts were combined, washed with sat. NaCl (100 mL), dried (MgSO4) and evaporated to dryness. The residue was subjected to silica-gel column chromatography [eluent: ethyl acetate/hexane, 30/70, v/v] to furnish decyl ether Compound 17 as a colourless oil. extracted with diethyl ether (3×250 mL) washed with sat. NaCl (100 mL) dried (MgSO4) evaporated to dryness

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 100 g (1 mole) of 1-methyl-piperazine and 176.5 g (1 mole) of decyl chloride were heated under reflux, at an external temperature of 150° C, until the reaction mixture had ceased boiling. After cooling, the solid product was extracted by shaking with a mixture with 40 g (1 mole) of sodium hydroxide in 500 ml of water and 500 ml of isobutanol. The organic phase was separated off and concentrated, and the residue was extracted with petroleum ether. After evaporating the petroleum ether solution, 180 g (75% of theory) of 1-methyl-4-decyl-piperazine were obtained in a form which was pure according to thin layer chromatography. After cooling the solid product was extracted The organic phase was separated off concentrated the residue was extracted with petroleum ether After evaporating the petroleum ether solution

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

Procedure: The desired product was prepared by substituting 4-hydroxy-1-naphthaldehyde and 1-chlorodecane for Example 20C and tert-butyl bromoacetate, respectively, in Example 20D.