tert-Butyl methyl ether → N-[3-(2-dimethylaminoethoxy)4-methoxyphenyl]aminoacetaldehyde dimethyl acetal

HRID 399269Notes

Reaction equation

HRID 399269 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[NH2:9].[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH:19]=O.C(OC)(C)(C)C>[Pd].C(O)C>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH:9][C:8]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:15])[CH3:1])[CH:7]=1

Participants

6

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 105603983-(2-(Dimethylamino)ethoxy)-4-methoxyaniline

Product 1

HCID 10590199N-[3-(2-dimethylaminoethoxy)4-methoxyphenyl]aminoacetaldehyde dimethyl acetalYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(2-dimethylaminoethoxy)-4-methoxyaniline (D11, 5.7 g, 0.027 mole) ethanol (120 ml) was treated with a solution of 2,2-dimethoxyacetaldehyde in methyl tert-butyl ether (9.5 g of approx. 40% solution, 0.036 mole) and kept at room temperature for 16 hours. The solution was then hydrogenated over 10% Pd-C (0.6 g) at atmospheric pressure and temperature for 7 hours. The catalyst was removed by filtration through kieselguhr and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed twice with water (2×60 ml), then dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5% methanol/chloroform to afford the title compound as a red oil (5.4 g, 67%).

Workup

  1. customThe catalyst was removed by filtration through kieselguhr
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  4. washwashed twice with water (2×60 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-31b811bd325943d3b666afdd3b277630
Source dataset
uspto-grants-1998_10
Patent number
US05817833

Reaction notes

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