2,2-Diethoxyethylamine → HCID 13911324, compound

HRID 1088922Notes

Reaction equation

HRID 1088922 reaction equation
[H][H].[CH3:3][O:4][C:5]1[C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=[CH:9][C:6]=1[CH:7]=O.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH2:21])[CH3:17]>C(O)C.[Pt]=O>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH:21][CH2:7][C:6]1[CH:9]=[CH:10][C:11]2[O:15][CH2:14][O:13][C:12]=2[C:5]=1[O:4][CH3:3])[CH3:17]

Participants

6

Reactant 3

HCID 695242,2-DiethoxyethylamineHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 13911324HCID 13911324, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent2×

Procedure

Platinum oxide was added in an amount of 1.0 g to 100 ml of ethanol, and hydrogen gas was passed through the mixture with stirring for 30 minutes. Then, 54.06 g (0.3 mol) of 2-methoxy-3,4-methylenedioxybenzaldehyde (1) and 40.78 g (0.3 mol) of aminoacetaldehyde diethylacetal (98% purity) in 100 ml of ethanol were added and hydrogenation was carried out while stirring the reaction mixture at room temperature for 8.5 hours. The catalyst was then removed by filtration and the solvent was distilled off at reduced pressure to obtain 89.43 g of N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (2) as an oil with 100% yield. IR and NMR of the resultant product are listed below.

Workup

  1. stirringwhile stirring the reaction mixture at room temperature for 8.5 hours
  2. customThe catalyst was then removed by filtration
  3. distillationthe solvent was distilled off at reduced pressure

Sources & evidence

ORD record
ord-fd3c6c1d060743f99f398c0b1cb415af
Source dataset
uspto-grants-1990_10
Patent number
US04963684

Reaction notes

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