Sodium hydride → HCID 131710608, compound

HRID 1704797Notes

Reaction equation

HRID 1704797 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[S:15](=[O:17])(=[O:16])[CH2:14][CH2:13][CH2:12][S:11]3(=[O:19])=[O:18])=[CH:4][C:3]=2[O:2]1.[H-].[Na+].[Cl:22][CH2:23][CH2:24][CH2:25][N:26](CCC1C=CC(OC)=C(OC)C=1)[CH3:27]>CN(C)C=O>[ClH:22].[CH3:27][NH:26][CH2:25][CH2:24][CH2:23][C:10]1([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[S:15](=[O:16])(=[O:17])[CH2:14][CH2:13][CH2:12][S:11]1(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 22758341HCID 22758341, compound

Product 1

HCID 131710608HCID 131710608, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.08 g of 2-(3,4-methylenedioxyphenyl)-m-dithiane-1,1,3,3-tetraoxide (prepared as described in Example 2) are stirred under argon with 25 ml of absolute dimethylformamide and treated with 0.8 g of a 55% sodium hydride suspension. The mixture is left to react for 0.5 hour at room temperature and for 1 hours at 40° C. After cooling to room temperature, 4.8 g of N-(3-chloropropyl)-3,4-dimethoxy-N-methyl-phenethylamine (prepared as described in Example 3) are added and the mixture is heated at 100° C. for 16 hours. The cooled mixture is then poured on to ice and extracted three times with ethyl acetate. The organic extracts are washed with water, dried over magnesium sulphate and evaporated in vacuo. The residual oil is dissolved in acetone and treated with 5 ml of a 6-N hydrogen chloride solution in dioxane. The precipitate, which is filtered off under a vacuum, is recrystallized from acetone. There are obtained 7.5 g of N-3,4-dimethoxyphenethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)-m-dithiane-2-propylamine- 1,1,3,3-tetraoxide hydrochloride of melting point 247°-248° C.

Workup

  1. waitThe mixture is left
  2. customto react for 0.5 hour at room temperature and for 1 hours at 40° C
  3. temperaturethe mixture is heated at 100° C. for 16 hours
  4. additionThe cooled mixture is then poured on to ice
  5. extractionextracted three times with ethyl acetate
  6. washThe organic extracts are washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated in vacuo
  9. dissolutionThe residual oil is dissolved in acetone
  10. additiontreated with 5 ml of a 6-N hydrogen chloride solution in dioxane
  11. filtrationThe precipitate, which is filtered off under a vacuum
  12. customis recrystallized from acetone

Sources & evidence

ORD record
ord-e21ce827d6554cc2b2ed0abe99ca44fd
Source dataset
uspto-grants-1978_11
Patent number
US04127588

Reaction notes

Loading…