4-Methyl-4-[2-(2-nitrophenoxy)ethyl]morpholin-4-ium methylsulfate → 4-[2-(2-Aminophenoxy)ethyl]-4-methylmorpholin-4-ium methylsulfate

HRID 2109962Notes

Reaction equation

HRID 2109962 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[CH3:7][N+:8]1([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[H][H]>C(O)C.[Pd]>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:14][N+:8]1([CH3:7])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 867608464-Methyl-4-[2-(2-nitrophenoxy)ethyl]morpholin-4-ium methylsulfateHCID 178418361HCID 178418361, compound

Product 1

HCID 867608484-[2-(2-Aminophenoxy)ethyl]-4-methylmorpholin-4-ium methylsulfate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2.08 g (5.5 mmol) of the compound from Step 5.2 was dissolved in 80 mL of ethanol and hydrogenated in the presence of 0.25 g of Pd/C (10%) under 9 bar of hydrogen pressure. After 2 hours, the catalyst was filtered off and the filtrate was evaporated to dryness. This gave 1.9 g (99% of the theoretical) of a colorless oil which was subjected to further reaction without additional purification.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThis gave 1.9 g (99% of the theoretical) of a colorless oil which was subjected to further reaction without additional purification

Sources & evidence

ORD record
ord-cd52688093b548a5b5225777d8682fef
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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