Ethanol → [4-(2-Morpholinoethoxy)phenyl]methylamine

HRID 613284Notes

Reaction equation

HRID 613284 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)C>Cl.O=[Pt]=O.C(Cl)(Cl)Cl>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 702EthanolHCID 29940744-(2-Morpholin-4-ylethoxy)benzonitrile

Product 1

HCID 7164631[4-(2-Morpholinoethoxy)phenyl]methylamineYield 79.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 345198Adams' catalystCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 4-[2-(4-morpholinyl)ethoxy]benzonitrile (0.93 g, 4 mmol), ethanol (100 mL), CHCl3 (4 mL) and PtO2 (100 mg) was hydrogenated at 45 psi on a Parr hydrogenator for 8 hours. Concentrated HCl (2-3 drops) was then added to the reaction mixture and the hydrogenation was continued for another 10 hours. The catalyst was removed by filtration, the filter cake was washed with ethanol and then the filtrate was evaporated to dryness. The residue was dissolved in water and then was saturated with solid K2CO3. The mixture was extracted with CH2Cl2 and then the CH2Cl2 layer was dried over K2CO3 and evaporated to afford 0.75 g (79%) of 4-[2-(4-morpholinyl)ethoxy]phenylmethylamine.

Workup

  1. waitthe hydrogenation was continued for another 10 hours
  2. customThe catalyst was removed by filtration
  3. washthe filter cake was washed with ethanol
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in water
  6. extractionThe mixture was extracted with CH2Cl2
  7. dry with materialthe CH2Cl2 layer was dried over K2CO3
  8. customevaporated

Sources & evidence

ORD record
ord-30f3825258264214a8d1299779c54a1d
Source dataset
uspto-grants-1999_12
Patent number
US06008226

Reaction notes

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