2-(1-ethylpiperidin-4-yl)ethanol

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

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

Procedure: Prepared similarly to Intermediate 20 from 3-(4-piperidinyl)-1-propanol hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (t, J=7.2 Hz, 3H) 1.01-1.23 (m, 5H) 1.36-1.45 (m, 2H) 1.56-1.63 (m, 2H) 1.72-1.81 (m, 2H) 2.22-2.29 (m, 2H) 2.73 (s, 17H residual DMF) 2.81 (d, J=11.54 Hz, 2H) 2.86-2.92 (m, 18H residual DMF) 3.30-3.39 (m, 3H) 4.30-4.36 (m, 1H) 7.95 (s, 8H residual DMF)

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

Procedure: Prepared similarly to Intermediate 19 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine and 2-(1-ethyl-4-piperidinyl)ethanol.

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

Procedure: Prepared similarly to Intermediate 19 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine and 2-(1-ethyl-4-piperidinyl)ethanol.

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

Procedure: To a stirring solution of 2-(4-piperidinyl)ethanol (1 g, 7.74 mmol) and potassium carbonate (2.67 g, 19.35 mmol) in dry DMF (10 ml) was added iodoethane (0.687 ml, 8.51 mmol). The reaction mixture was allowed to stir at room temperature for 18 hours. The solvent was partially removed in vacuo and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The aqueous was washed with further ethyl acetate and the combined organics dried (hydrophobic frit) and concentrated in vacuo to give the title compound as a mixture with residual DMF as a clear oil, 1.55 g The solvent was partially removed in vacuo the residue partitioned between water (20 ml) and ethyl acetate (20 ml) The aqueous was washed with further ethyl acetate the combined organics dried (hydrophobic frit) concentrated in vacuo

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

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

Procedure: Prepared similarly to Intermediate 20 from 3-(4-piperidinyl)-1-propanol hydrochloride.

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

Procedure: Prepared similarly to Intermediate 19 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine and 2-(1-ethyl-4-piperidinyl)ethanol.

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

Procedure: Prepared similarly to Intermediate 19 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine and 2-(1-ethyl-4-piperidinyl)ethanol.

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

Procedure: To a stirring solution of 2-(4-piperidinyl)ethanol (Ig, 7.74 mmol) and potassium carbonate (2.67 g, 19.35 mmol) in dry DMF (10 ml) was added iodoethane (0.687 ml, 8.51 mmol). The reaction mixture was allowed to stir at room temperature for 18 hours. The solvent was partially removed in vacuo and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The aqueous was washed with further ethyl acetate and the combined organics dried (hydrophobic frit) and concentrated in vacuo to give the title compound as a mixture with residual DMF as a clear oil, 1.55 g The solvent was partially removed in vacuo the residue partitioned between water (20 ml) and ethyl acetate (20 ml) The aqueous was washed with further ethyl acetate the combined organics dried (hydrophobic frit) concentrated in vacuo

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

Procedure: To a stirring solution of 2-(4-piperidinyl)ethanol (Ig, 7.74 mmol) and potassium carbonate (2.67 g, 19.35 mmol) in dry DMF (10 ml) was added iodoethane (0.687 ml, 8.51 mmol). The reaction mixture was allowed to stir at room temperature for 18 hours. The solvent was partially removed in vacuo and the residue partitioned between water (20 ml) and ethyl acetate (20 ml). The aqueous was washed with further ethyl acetate and the combined organics dried (hydrophobic frit) and concentrated in vacuo to give the title compound as a mixture with residual DMF as a clear oil, 1.55 g The solvent was partially removed in vacuo the residue partitioned between water (20 ml) and ethyl acetate (20 ml) The aqueous was washed with further ethyl acetate the combined organics dried (hydrophobic frit) concentrated in vacuo

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

Procedure: Prepared similarly to Intermediate 20 from 3-(4-piperidinyl)-1-propanol hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (t, J=7.2 Hz, 3H) 1.01-1.23 (m, 5H) 1.36-1.45 (m, 2H) 1.56-1.63 (m, 2H) 1.72-1.81 (m, 2H) 2.22-2.29 (m, 2H) 2.73 (s, 17H residual DMF) 2.81 (d, J=11.54 Hz, 2H) 2.86-2.92 (m, 18H residual DMF) 3.30-3.39 (m, 3H) 4.30-4.36 (m, 1H) 7.95 (s, 8H residual DMF)