4-(2-(Benzyloxy)ethyl)morpholin-3-one → 4-(2-Hydroxyethyl)morpholin-3-one

HRID 601532Notes

Reaction equation

HRID 601532 reaction equation
C([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][C:12]1=[O:17])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][C:12]1=[O:17]

Participants

4

Reactant 1

HCID 574214944-(2-(Benzyloxy)ethyl)morpholin-3-one

Product 1

HCID 152874004-(2-Hydroxyethyl)morpholin-3-oneYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 4-(2-benzyloxy-ethyl)-morpholin-3-one (1.7 g, 7.23 mmol) in ethanol (25 mL) and add 5% Pd/C (0.30 g). Hydrogenate at 60 psi overnight, filter the black mixture through Celite®, and wash the Celite® with additional ethanol (approximately 10 mL). Concentrate the filtrate to give the title compound as an oil (0.7 g, 70%). MS (ES+) 146.3 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 4.11 (s, 2H), 3.83 (t, 2H, J=5.1 Hz), 3.73 (t, 2H, J=5.3 Hz), 3.49 (t, 2H, J=5.3 Hz), 3.43 (t, 2H, J=5.1 Hz), 3.12 (s, 1H).

Workup

  1. filtrationHydrogenate at 60 psi overnight, filter the black mixture through Celite®
  2. washwash the Celite® with additional ethanol (approximately 10 mL)
  3. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-5941c8285ef34aa6b1ce6f2904012010
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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