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

HRID 1458749Notes

Reaction equation

HRID 1458749 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) is hydrogenated at 45 psi on a Parr hydrogenator for 8 hours. Concentrated HCl (2-3 drops) is then added to the reaction mixture, and the hydrogenation is continued for another 10 hours. The catalyst is removed by filtration, the filter cake is washed with ethanol and then the filtrate is evaporated to dryness. The residue is dissolved in water and then is saturated with solid K2CO3. The mixture is extracted with CH2Cl2 and then the CH2Cl2 layer is dried over K2CO3 and evaporated to afford 0.75 g (79%) of 4-[2-(4-morpholinyl)ethoxy]phenylmethylamine.

Workup

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

Sources & evidence

ORD record
ord-1b7dbb0f13904c3bb21b074fb4755c3e
Source dataset
uspto-grants-1998_12
Patent number
US05852035

Reaction notes

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