Sulfuric Acid → HCID 13912214, compound

HRID 845831Notes

Reaction equation

HRID 845831 reaction equation
[CH2:1]([O:3][CH:4](OCC)[CH2:5][N:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[C:10]=1[O:18][CH3:19])[CH3:7])[CH3:2].S(=O)(=O)(O)O.[OH-].[Na+]>C(O)C>[OH:3][CH:4]1[C:14]2[C:9](=[C:10]([O:18][CH3:19])[C:11]3[O:17][CH2:16][O:15][C:12]=3[CH:13]=2)[CH2:8][N:6]([CH3:7])[CH2:5]1.[CH2:1]([O:3][CH:4]1[C:14]2[C:9](=[C:10]([O:18][CH3:19])[C:11]3[O:17][CH2:16][O:15][C:12]=3[CH:13]=2)[CH2:8][N:6]([CH3:7])[CH2:5]1)[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 139122132,2-Diethoxy-N-((4-methoxybenzo[D][1,3]dioxol-5-YL)methyl)-N-methylethan-1-amine

Product 2

HCID 13912214HCID 13912214, compoundYield 61%HCID 13912215HCID 13912215, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

780 mg (2.5 mmol) of N-(2-methoxy-3,4-methylenedioxybenzyl)-N-methylaminoacetaldehyde diethylacetal (3) was dissolved in 1.6 ml of ethanol. The solution was added with 5 ml of 6N sulfuric acid and refluxed under heating for 2 hours and 45 minutes. After cooling, this solution was made basic by adding a 25% aqueous solution of sodium hydroxide and extracted with 5 ml and then with 2 ml of methylene chloride successively. The extracts were joined, washed with 2 ml of water and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was separated by silica gel column chromatography to obtain 360 mg of 4-hydroxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (6) (yield: 61%) and 110 mg of 4-ethoxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (8) (yield: 17%).

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours and 45 minutes
  3. temperatureAfter cooling
  4. extractionextracted with 5 ml
  5. washwashed with 2 ml of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-04b92a86c8e64801830e439c57c2c2c8
Source dataset
uspto-grants-1988_07
Patent number
US04760145

Reaction notes

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