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

HRID 601557Notes

Reaction equation

HRID 601557 reaction equation
C([N:8]1[CH2:13][C:12]([CH3:15])([CH3:14])[O:11][C:10]([CH3:17])([CH3:16])[CH2:9]1)C1C=CC=CC=1>CCO.[Pd]>[CH3:16][C:10]1([CH3:17])[O:11][C:12]([CH3:15])([CH3:14])[CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 1

HCID 122829994-Benzyl-2,2,6,6-tetramethylmorpholine

Product 1

HCID 198280762,2,6,6-TetramethylmorpholineYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  1. filtrationFilter the mixture
  2. customto remove Pd catalyst
  3. additiontreat the filtrate with 2M HCl in ether
  4. concentrationconcentrate
  5. customDry the residue at 80° C. under vacuum

Sources & evidence

ORD record
ord-6f668bf5a929481596c3cac4e1c9f699
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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