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

HRID 622200Notes

Reaction equation

HRID 622200 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[C:5]=1[O:13][CH3:14].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][N:2]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[C:5]=1[O:13][CH3:14])[CH3:1]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 816722-Bromo-1,1-dimethoxyethaneHCID 21294019N-methyl-2-methoxy-3,4-methylenedioxybenzylamine

Product 1

HCID 14609557N-(2,2-Dimethoxyethyl)-4-methoxy-N-methyl-1,3-benzodioxole-5-methanamineYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

0.98 g of N-methyl-(2-methoxy-3,4-methylenedioxybenzylamine obtained in Example 14, 0.93 g (1.1 equivalent) of bromoacetaldehyde dimethylacetal and 0.76 g (1.5 equivalent) of triethylamine as base were mixed in 7.3 ml of toluene and heated under reflux for 4 hours. On cooling the reaction mixture to room temperature, the deposited salts were filtered out and the toluene layer was analyzed to show that 1.302 g of the desired N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde dimethylacetal was obtained. Yield 92%. Because 0.25 g of excessive triethylamine was present in the toluene layer, a toluene solution of the desired N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde dimethylacetal was obtained by distilling off excessive triethylamine at atmospheric pressure.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe deposited salts were filtered out
  4. customwas obtained

Sources & evidence

ORD record
ord-daa8e256c7f94ef1b6addd2bf602f813
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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