4-Methylmorpholine → HCID 10564036, compound

Participants

Reaction Steps

A suspension of 4-(4-phenylphenoxy)butanoic acid (2.42 g, 9.45 mmol) in thionyl chloride (25 mL) was heated at reflux for 90 minutes, during which time the mixture became homogenous. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was taken up in 1:1 methylene chloride/THF. In a separate flask 4-methylmorpholine (3.5 mL, 32 mmol) was added to a solution of hydroxylamine hydrochloride (2.1 g, 30 mmol) in water (10 mL). THF (20 mL) was then added and the hydroxylamine solution was decanted into the acid chloride solution, and the reaction mixture was vigorously stirred for 2 hours. The reaction mixture was partitioned between saturated aqueous NH4Cl and methylene chloride. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-(4-phenylphenoxy)butanohydroxamic acid (1.45 g) as a white solid. 1H NMR (DMSO-d6) δ 1.94 (m, 2H), 2.14 (t, 2H, J=7 Hz), 4.01 (t, 2H, J=6 Hz), 7.02 (d, 2H, J=8 Hz), 7.29 (t, 1H, J=6 Hz), 7.43 (t, 2H, J=6 Hz), 7.62 (m, 4H), 8.71 (s, 1H), 10.44 (s, 1H). MS (DCI/NH3) 289 (M+NH4+, 100), 272 (M+H+, 35), 255 (30). Anal. Calcd for: C16H17NO3 : C, 70.83; H, 6.32; N, 5.16. Found: C, 64.81; H, 6.65; N, 5.82.

Provenance & Evidence