4-phenoxybutan-1-ol

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

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.

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

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.

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

Procedure: 4-Phenoxy-1-butanol (4 g), 1,6-dibromohexane (6.7 ml), TAB (0.8 g) and sodium hydroxide (9.4 g in 18 ml water) were stirred at room temperature under nitrogen for 20 h. Water (80 ml) was added and the mixture extracted with diethyl ether (3×100 ml). The combined organic extracts were washed with water (50 ml), brine (50 ml), dried and evaporated to give a colourless liquid. This was applied to an FCC column and eluted with cyclohexane (2 l) and then with System A (1:40). The resulting oil was distilled to give the title compound (3.4 g) as a colourless oil b.p. 150°/3.5 mmHg T.l.c. (System A 1:6) Rf 0.3. the mixture extracted with diethyl ether (3×100 ml) The combined organic extracts were washed with water (50 ml), brine (50 ml) dried evaporated to give a colourless liquid eluted with cyclohexane (2 l) The resulting oil was distilled

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.

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

Procedure: The title compound was prepared by procedures of Example 16 from sulfamoyl chloride and 4-phenoxy-1-butanol in 54% yield as an off-white solid, mp 76°-77° C.

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

Procedure: The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-(4-phenoxybutoxy)pyrazine (1.99 g, 7.14 mmol; obtained according to the procedure of example 50, step 1, starting from 4-phenoxy-1-butanol*), piperazine (1.84 g, 21.4 mmol) and K2CO3 (0.99 g, 7.14 mmol). The yield of the title compound was 1.52 g (65%) which was obtained as an oil. Purity100% (HPLC). MS m/z 329 (M+H)+. HRMS m/z calcd for C18H24N4O2 (M)+ 328.1899, found 328.1894. The title compound was prepared obtained was obtained as an oil

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

Procedure: The title compound was prepared according to the procedure of example 50, step 2, starting from 2-chloro-6-(4-phenoxybutoxy)pyrazine (1.99 g, 7.14 mmol; obtained according to the procedure of example 50, step 1, starting from 4-phenoxy-1-butanol*), piperazine (1.84 g, 21.4 mmol) and K2CO3 (0.99 g, 7.14 mmol). The yield of the title compound was 1.52 g (65%) which was obtained as an oil. Purity 100% (HPLC). MS m/z 329 (M+H)+. HRMS m/z calcd for C18H24N4O2 (M)+ 328.1899, found 328.1894. *Prepared by reduction (LiAlH4) of the corresponding acid (cf J. Org. Chem. 1965, 30, 2441-2447; ibid. 1968, 33, 2271-2284). The title compound was prepared obtained was obtained as an oil

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

Procedure: The title compound was prepared by the procedure of Preparation 2 in 91% yield from 4-phenoxy-1-butanoic acid and lithium aluminum hydride.