4-(morpholin-4-ylmethyl)phenol

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:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-(morpholinomethyl)phenol (776 mg, 4.0 mmol) and N-(6-bromohexyl)phthalimide (1.24 g, 4.0 mmol) in DMF (10 mL) was added K2CO3 over 2 min. The reaction was heated to 90° C. for 3 h, then stirred at r.t. overnight. The mixture was concentrated and water (10 mL) added. This was extracted with ether (3×30 mL) and the combined organics washed with pH 7 phosphate buffer (20 mL), dried with Na2SO4, and concentrated to give the title compound as a clear oil. The mixture was concentrated water (10 mL) added This was extracted with ether (3×30 mL) the combined organics washed with pH 7 phosphate buffer (20 mL) dried with Na2SO4 concentrated

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

Procedure: To a solution of 4-(morpholinomethyl)phenyl acetate (1.9 g, 8.1 mmol) in 1:1 methanol/water (40 mL) at 0° C. was added LiOH.H2O (339 mg, 8.1 mmol). The reaction was stirred at RT for 2 h. The mixture was concentrated to remove methanol, and the aqueous layer acidified with 3 N HCl. The aqueous layer was extracted with ethyl acetate (4×30 mL) and the organics dried and concentrated to give 454 mg recovered starting material. The aqueous layer was then made basic again (to pH 9) with 1 N NaOH and extracted with ethyl acetate (7×20 mL). These combined organics were washed with brine, dried with Na2SO4, and concentrated to give a white solid. The mixture was concentrated to remove methanol The aqueous layer was extracted with ethyl acetate (4×30 mL) the organics dried concentrated to give 454 mg recovered extracted with ethyl acetate (7×20 mL) These combined organics were washed with brine dried with Na2SO4 concentrated to give a white solid