Acetaldehyde, 2,2-dimethoxy- → HCID 21467216, compound

HRID 1939224Notes

Reaction equation

HRID 1939224 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1.[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH:20]=O>C(O)C.[Pd]>[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20][NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]2)[CH:5]=1

Participants

5

Reactant 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 21467216HCID 21467216, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 4-methoxy-3-(4-methyl-1-piperazinyl) benzenamine (5 g, 0.023 mol) in ethanol (150 ml) and dimethoxyethanal (9.5 g, 1.2 eq) was hydrogenated over 10% Palladium on charcoal (3 g) at standard temperature and pressure for 3 h. The suspension was filtered through kieselguhr, washed with methanol and evaporated to give a pale yellow oil. Purification by Fcc, eluting with 2% methanol/dichloromethane afforded the title compound (6.64 g, 95%).

Workup

  1. filtrationThe suspension was filtered through kieselguhr
  2. washwashed with methanol
  3. customevaporated
  4. customto give a pale yellow oil
  5. customPurification by Fcc
  6. washeluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-cad148a082c8404a99f8106de3af44ae
Source dataset
uspto-grants-1997_12
Patent number
US05696122

Reaction notes

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