4-Benzyl-2,2,6,6-tetramethylmorpholine → 2,2,6,6-Tetramethylmorpholine

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Reaction Steps

Dissolve 4-benzyl-2,2,6,6-tetramethylmorpholine (Bennett, G. B.; Houlihan, W. J.; Mason, R. B.; Engstrom, R. G. J. Med. Chem. 1976, 19, 709-714) (11.0 g, 47.1 mmol) in EtOH (650 mL) and add 3% Pd/C (8.61 g). Shake the mixture under hydrogen (60 psi) at 40° C. for 24 h. Filter the mixture to remove Pd catalyst, and treat the filtrate with 2M HCl in ether, then concentrate. Dry the residue at 80° C. under vacuum to give the title compound (6.79 g) as a white solid. 1H NMR (DMSO-d6, 400 MHz) δ 9.8 (2H, br s), 2.88 (4H, s), 1.25 (12H, s).

Provenance & Evidence