2,2-Diethoxyethylamine → HCID 13911324, compound

HRID 845827Notes

Reaction equation

HRID 845827 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

One g of platinum oxide was added to 100 ml of ethanol, and hydrogen was passed through the solution under stirring for 30 minutes. To this solution was added a solution of 54.06 g (0.3 mol) of 2-methoxy-3,4-methylenedioxybenzaldehyde (1) and 40.78 g (0.3 mol) of aminoacetaldehyde diethylacetal (2) (purity: 98%) in 100 ml of ethanol to carry out hydrogenation under stirring at room temperature for 8.5 hours. Then the catalyst was filtered out and the solvent was distilled off under reduced pressure to obtain 89.43 g of N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (2) as an oil (yield: 100%).

Workup

  1. stirringunder stirring at room temperature for 8.5 hours
  2. filtrationThen the catalyst was filtered out
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-8bfe5b295c2840d8a203c5de510dd8c6
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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