Butylamine → Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate

HRID 1269666Notes

Reaction equation

HRID 1269666 reaction equation
[CH2:1]([C:3]1[CH:15]=[C:14]([CH:16]=O)[CH:13]=[CH:12][C:4]=1[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[CH2:18]([NH2:22])[CH2:19][CH2:20][CH3:21]>C(O)C>[CH2:18]([NH:22][CH2:16][C:14]1[CH:13]=[CH:12][C:4]([O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]([CH2:1][CH3:2])[CH:15]=1)[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 58622859Ethyl (2-ethyl-4-formylphenoxy)acetate

Product 1

HCID 58622897Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetateYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (2-ethyl-4-formylphenoxy)acetate (0.52 g, 2.2 mmol) in anhydrous ethanol (10 mL) was added butylamine (0.26 mL, 2.6 mmol). The resulting solution was stirred at room temperature under N2 for 18 h over 4A molecular sieves. The reaction was quenched by cautious addition of sat. NaHCO3 aq. (30 mL) and the mixture stirred for 30 mins. The mixture was then extracted EtOAc (2×100 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification by SPE (SCX, 20 g) conditioning the cartridge with ethanol and then loading the compound and washing with CH2Cl2, then ethanol before eluting the title compound using 10% NH3 in ethanol, evaporation of the 10% NH3 in ethanol extract afforded the title compound as a pale yellow oil (0.364 g).

Workup

  1. customThe reaction was quenched by cautious addition of sat. NaHCO3 aq. (30 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by SPE (SCX, 20 g) conditioning the cartridge with ethanol
  6. washwashing with CH2Cl2
  7. washethanol before eluting the title compound
  8. custom10% NH3 in ethanol, evaporation of the 10% NH3 in ethanol
  9. extractionextract

Sources & evidence

ORD record
ord-0ec592b03c4a40a1a5f42e1e8892965e
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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