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

HRID 622192Notes

Reaction equation

HRID 622192 reaction equation
[CH2:1]([O:3][CH:4]([O:29][CH2:30]C)[CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[C:19]=1[O:27][CH3:28])S(C1C=CC(C)=CC=1)(=O)=O)C.Cl.[CH2:33](O)C>[Pd]>[CH3:30][O:29][CH:4]([O:3][CH3:1])[CH2:5][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]2[O:24][CH2:25][O:26][C:20]=2[C:19]=1[O:27][CH3:28])[CH3:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13911325N-(2-methoxy-3,4-methylenedioxybenzyl)-N-(p-toluenesulfonyl)aminoacetaldehyde diethylacetal

Product 1

HCID 14609557N-(2,2-Dimethoxyethyl)-4-methoxy-N-methyl-1,3-benzodioxole-5-methanamineYield 56%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

7.81 g (40 mmol) of 2-methoxy-3,4-methylenedioxybenzaldoxime (2) thus obtained, 3.67 ml (44 mmol) of concentrated hydrochloric acid and 500 mg of 5% palladium on carbon catalyst were added to 80 ml of ethanol to carry out hydrogenation at room temperature for 4 hours and 45 minutes. The catalyst was filtered out, the filtrate was concentrated and the residue is recrystallized from 60 ml of ethanol to obtain 4.86 g of 2-methoxy-3,4-methylenedioxybenzylamine hydrochloride (3). Yield 56%, m.p. 208°-210° C. IR and NMR spectra of the resultant product are listed below. ##STR29##

Workup

  1. customat room temperature
  2. customfor 4 hours
  3. custom45 minutes
  4. filtrationThe catalyst was filtered out
  5. concentrationthe filtrate was concentrated
  6. customthe residue is recrystallized from 60 ml of ethanol

Sources & evidence

ORD record
ord-25af32726eea4c73bc3460df724fad16
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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