[2-(2-morpholin-4-ylethoxy)phenyl]methanol

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: Thionyl chloride (5 mL, 2M in DCM) was added to a solution of [2-(2-morpholin-4-yl-ethoxy)-phenyl]-methanol (1.97 g, 8.3 mmol) in DCM (15 mL) at 0° C. The mixture was allowed to warm up to rt and stirred for 3 hours. The reaction was concentrated to give 4-[2-(2-chloromethyl-phenoxy)-ethyl]-morpholine hydrochloride. The reaction was concentrated

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

Procedure: A mixture of 2-hydroxybenzyl alcohol (1.295 g, 10.4 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.94 g, 10.4 mmol) in 2N NaOH (10.5 mL) was stirred at rt for 14 hours. The precipitate was collected by vacuum filtration, washed with 1N NaOH, redissolved in DCM and washed with 1N NaOH. The aqueous layer was extracted with more DCM (2×). The combined DCM was dried and concentrated to give [2-(2-morpholin-4-yl-ethoxy)-phenyl]-methanol which was used without further purification. The precipitate was collected by vacuum filtration washed with 1N NaOH redissolved in DCM washed with 1N NaOH The aqueous layer was extracted with more DCM (2×) The combined DCM was dried concentrated