Formaldehyde → N-(2,2-Dimethoxyethyl)-4-methoxy-N-methyl-1,3-benzodioxole-5-methanamine

HRID 845828Notes

Reaction equation

HRID 845828 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.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][NH2:20].[CH2:23]=O>C(O)C.[Pt]=O.CO>[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19][N:20]([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])[CH3:23]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 101979461,3-Benzodioxole-5-carboxaldehyde, 4-methoxy-HCID 178418361HCID 178418361, compound

Product 1

HCID 14609557N-(2,2-Dimethoxyethyl)-4-methoxy-N-methyl-1,3-benzodioxole-5-methanamineYield 99.1%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 20 ml of methanol, 0.2 g of platinum oxide was added and then hydrogen was passed through the solution to activate the catalyst. To the solution was added a solution of 10.81 g (60 mmol) of 2-methoxy-3,4-methylenedioxybenzaldehyde (1) and 6.37 g (60 mmol) of aminoacetaldehyde dimethylacetal (99% purity) in 20 ml of ethanol to carry out hydrogenation for 3.5 hours. Then, 5.24 ml of 35% formaline (66 mmol) was added to carry out further hydrogenation for 9 hours. The catalyst was filtered out and the filtrate was concentrated under reduced pressure to obtain 16.85 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde dimethylacetal (5) as an oil. Yield: 99%.

Workup

  1. customfor 3.5 hours
  2. customfor 9 hours
  3. filtrationThe catalyst was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2611f0b70502447283be8a13d1376d98
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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