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

HRID 622198Notes

Reaction equation

HRID 622198 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.O.[OH-].[Na+].[CH2:35](Cl)Cl>>[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])[CH3:35]

Participants

5

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 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 99.7%

Procedure

17.8 g (74.3 mmol) of the compound (2) thus obtained was added to 50 ml of water, to which 100 ml of methylene chloride was added. This solution was made basic with 25% aqueous solution of sodium hydroxide under water-cooling. The solution was separated and the aqueous layer was extracted with 20 ml of methylene chloride. The obtained methylene chloride layers were combined, washed with 30 ml of water, dried over anhydrous magnesium sulfate and then concentrated under vacuum to obtain 15.06 g of 8-methoxy-6,7-methylenedioxyisoquinoline (3) (yield 99.7%). The product thus obtained was recrystallized from ethylacetate-n-hexane, m.p. 144°-5° C. IR and NMR spectra of the resultant product are listed below. ##STR48##

Workup

  1. additionwas added
  2. temperaturecooling
  3. customThe solution was separated
  4. extractionthe aqueous layer was extracted with 20 ml of methylene chloride
  5. washwashed with 30 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-be23a90f2ef54c33add335383e7cbb18
Source dataset
uspto-grants-1988_09
Patent number
US04769480

Reaction notes

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