4-Benzyl-2-[(pyrrolidin-1-yl)methyl]morpholine → 2-[(Pyrrolidin-1-yl)methyl]morpholine

HRID 2112765Notes

Reaction equation

HRID 2112765 reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[Pd+2].[OH-].[C]>[N:15]1([CH2:14][CH:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 230796524-Benzyl-2-[(pyrrolidin-1-yl)methyl]morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 146275022-[(Pyrrolidin-1-yl)methyl]morpholineYield 95%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 702EthanolSolvent

Procedure

4-Benzyl-2-(pyrrolidin-1-ylmethyl)morpholine (450 mg, 1.73 mmol) prepared according to Process Step 1 was dissolved in ethanol (10 mL), and 20% palladium hydroxide-carbon (200 mg, 0.285 mmol) was suspended therein, followed by stirring under the hydrogen gas atmosphere for two days. Celite (registered trademark: 2.0 g) was suspended in the reaction mixture, the solid was separated by filtration, and the solvent was distilled off under reduced pressure from the filtrate. The residue was purified by silica gel column chromatography (chloroform:methanol=5:1) and thereby yielded 2-(pyrrolidin-1-ylmethyl)morpholine (280 mg, in a yield of 95%).

Workup

  1. customthe solid was separated by filtration
  2. distillationthe solvent was distilled off under reduced pressure from the filtrate
  3. customThe residue was purified by silica gel column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-30b2270cd7874924b757e81fbc774dac
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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