4-(4-aminophenyl)butan-1-ol

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-(p-amino phenyl) butanol (2 g in 125 mL of ethyl ether) is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 3 h at room temperature, cooled at -20° C., and faltered. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated and recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6): 8.65 (s, 1p, ArNH), 7.4-7.0 (dd, 4p, p-substituted Ar), 6.4 (broad t, 1p, NHCH2), 3.7-3.4 (m, 6p, ArCH2 and NHCH2CH2Cl), 2.85 (t, 2p, CH2OH), 2.3 (s, 1p, CH2OH), 1.85 (q, 2p, CH2CH2CH2), 1.45 (q, 2p, CH2CH2OH) cooled at -20° C. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet)

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

Procedure: To a solution of 4-(p-amino phenyl) butanol (2 g in 125 mL of ethyl ether) is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 3 h at room temperature, cooled at -20° C., and faltered. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated and recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6): 8.65 (s, 1p, ArNH), 7.4-7.0 (dd, 4p, p-substituted Ar), 6.4 (broad t, 1p, NHCH2), 3.7-3.4 (m, 6p, ArCH2 and NHCH2CH2Cl), 2.85 (t, 2p, CH2OH), 2.3 (s, 1p, CH2OH), 1.85 (q, 2p, CH2CH2CH2), 1.45 (q, 2p, CH2CH2OH) cooled at -20° C. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet)

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

Procedure: 4-(4-nitrophenyl)butanol (compound 19, 1.7 mL, 10.2 mmol) was dissolved in methanol (20 mL) to which 10% Palladium on carbon (0.2 g) was added and the mixture was hydrogenated using hydrogen gas (30 psi) at ambient temperature for 1 hr. The mixture was filtered through celite filter aid and solvent was evaporated from the filtrate under vacuum to give 1.3 g (77% yield) of crude product. Mass spectrum (M+H)+ calcd for C10H15NO 166.1. found 166.1. was added at ambient temperature for 1 hr The mixture was filtered through celite filter aid and solvent was evaporated from the filtrate under vacuum

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

Procedure: A mixture of 4-aminobenzenebutanol (7.5), 2-chloroethyl ether (6.5 g, 5.32 ml), DEA (11.74 g) and finely ground potassium iodide (15.0 g) was stirred in DMF (500 ml) at 100° under nitrogen for 65 h. The mixture was cooled, the solvent removed in vacuo at 55° and the residue partitioned between EA (250 ml) and water (100 ml). The aqueous layer was extracted with further EA (100 ml), the combined organic solutions washed with brine (150 ml), dried and evaporated onto FCC silica (15 g). The impregnated material was applied to an FCC column, elution with ER-CX (2:1) affording the title compound as a waxy cream solid (6.13 g) m.p. 51°-52°. The mixture was cooled the solvent removed in vacuo at 55° the residue partitioned between EA (250 ml) and water (100 ml) The aqueous layer was extracted with further EA (100 ml) the combined organic solutions washed with brine (150 ml) dried evaporated onto FCC silica (15 g) The impregnated material was applied to an FCC column, elution with ER-CX (2:1)

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

Procedure: A mixture of 4-aminobenzenebutanol (7.5), 2-chloroethyl ether (6.5 g, 5.32 ml), DEA (11.74 g) and finely ground potassium iodide (15.0 g) was stirred in DMF (500 ml) at 100° under nitrogen for 65 h. The mixture was cooled, the solvent removed in vacuo at 55° and the residue partitioned between EA (250 ml) and water (100 ml). The aqueous layer was extracted with further EA (100 ml), the combined organic solutions washed with brine (150 ml), dried and evaporated onto FCC silica (15 g). The impregnated material was applied to an FCC column, elution with ER-CX (2:1) affording the title compound as a waxy cream solid (6.13 g) m.p. 51°-52°. The mixture was cooled the solvent removed in vacuo at 55° the residue partitioned between EA (250 ml) and water (100 ml) The aqueous layer was extracted with further EA (100 ml) the combined organic solutions washed with brine (150 ml) dried evaporated onto FCC silica (15 g) The impregnated material was applied to an FCC column, elution with ER-CX (2:1)

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

Procedure: To a solution of 4-(p-amino phenyl) butanol (2 g in 125 mL of ethyl ether) is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 3 h at room temperature, cooled at -20° C., and faltered. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated and recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6): 8.65 (s, 1p, ArNH), 7.4-7.0 (dd, 4p, p-substituted Ar), 6.4 (broad t, 1p, NHCH2), 3.7-3.4 (m, 6p, ArCH2 and NHCH2CH2Cl), 2.85 (t, 2p, CH2OH), 2.3 (s, 1p, CH2OH), 1.85 (q, 2p, CH2CH2CH2), 1.45 (q, 2p, CH2CH2OH) cooled at -20° C. A white solid of 4-{p-[3-(2-chloroethyl)ureido]phenyl}butanol is separated recrystallized from ethanol (white flakes), yield 55%, mp 123°-124° C., IR (KBr pellet)

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.25 g (0.056 mole) 4-aminobenzenebutanol is dissolved in 100 ml pyridine and the solution is cooled to ca. -10° C. 17.33 ml (25.65 g) (0.244 mole) methanesulfonyl chloride is added dropwise with vigorous stirring at a rate such that the reaction temperature does not rise beyond -5° C. After all methanesulfonyl chloride is added, the reaction mixture is left in the freezer for two days. The reaction mixture is poured onto 300 ml ice water and extracted with 3×200 ml methylene chloride. The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions. The organic layer is dried over sodium sulfate, filtered, and stripped. The residue is crystallized from ethyl acetate/ether to obtain the title compound. does not rise beyond -5° C extracted with 3×200 ml methylene chloride The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions The organic layer is dried over sodium sulfate filtered The residue is crystallized from ethyl acetate/ether

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

Procedure: A mixture of 4-(4-nitro-phenyl)-butan-1-ol (2.0 g, 1.02 mmol), palladium on carbon (100 mg, 10%) and ethanol (25 ml) was treated with hydrogen gas on a Parr shaker (50 psi) for 1 hour. The mixture was filtered through a pad of celite under suction and the filtrate was concentrated under reduced pressure to afford 4-(4-amino-phenyl)-butan-1-ol (100% yield). The mixture was filtered through a pad of celite under suction the filtrate was concentrated under reduced pressure

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

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.25 g (0.056 mole) 4-aminobenzenebutanol is dissolved in 100 ml pyridine and the solution is cooled to ca. -10° C. 17.33 ml (25.65 g) (0.244 mole) methanesulfonyl chloride is added dropwise with vigorous stirring at a rate such that the reaction temperature does not rise beyond -5° C. After all methanesulfonyl chloride is added, the reaction mixture is left in the freezer for two days. The reaction mixture is poured onto 300 ml ice water and extracted with 3×200 ml methylene chloride. The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions. The organic layer is dried over sodium sulfate, filtered, and stripped. The residue is crystallized from ethyl acetate/ether to obtain the title compound. does not rise beyond -5° C extracted with 3×200 ml methylene chloride The combined organic layers are washed with 1 liter cold 5% HCl in 3 portions The organic layer is dried over sodium sulfate filtered The residue is crystallized from ethyl acetate/ether