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

HRID 622190Notes

Reaction equation

HRID 622190 reaction equation
[H][H].[CH2:3]([O:5][CH:6]([O:21][CH2:22]C)[CH2:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[C:11]=1[O:19][CH3:20])C.[CH3:24]OC(OC)CN.C=O>[Pt]=O.CO>[CH3:22][O:21][CH:6]([O:5][CH3:3])[CH2:7][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[C:11]=1[O:19][CH3:20])[CH3:24]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 89728Aminoacetaldehyde dimethyl acetalHCID 13911324HCID 13911324, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent2×

Procedure

0.2 g of platinum oxide catalyst was added to 20 ml of methanol, through which hydrogen was passed to activate the catalyst. 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 methanol were added to carry out hydrogenation for 3.5 hours. Then, 5.24 ml (66 mmol) of 35% formalin was added to carry out hydrogenation for 9 hours. The catalyst was filtered out and the filtrate was concentrated under vacuum to obtain 16.85 g of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde dimethylacetal (3) as an oil (yield 99%). IR and NMR spectra of the resultant product are listed below. ##STR24##

Workup

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

Sources & evidence

ORD record
ord-a110c532d66d4f2b8b333bcb0f458e77
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

Loading…