2,2-Diethoxyethylamine → HCID 13911324, compound

HRID 622189Notes

Reaction equation

HRID 622189 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]>[Pt]=O.C(O)C>[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 gram of platinum oxide catalyst was added to 100 ml of ethanol, through which hydrogen was passed 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 to carry out hydrogenation with stirring at room temperature for 8.5 hours. The catalyst was filtered out and the solvent was distilled off under vacuum to obtain 89.43 g of N-(2-methoxy-3,4-methylenedioxybenzyl)aminoacetaldehyde diethylacetal (2) (yield 100 %) as an oil. IR and NMR spectra of the resultant product are listed below. ##STR20##

Workup

  1. stirringwith stirring at room temperature for 8.5 hours
  2. filtrationThe catalyst was filtered out
  3. distillationthe solvent was distilled off under vacuum

Sources & evidence

ORD record
ord-d586d3aa1ea747ffada5527011919678
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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