Dimethyl Sulfoxide → HCID 86734431, compound

HRID 616309Notes

Reaction equation

HRID 616309 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[S:10](=[O:11])[CH2:9][CH2:8][CH2:7][S:6]1=[O:12].[CH3:23][NH:24][CH2:25][CH2:26][C:27]1[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[C:29]([O:30][CH3:31])[CH:28]=1.CS(C)=O>O>[ClH:1].[CH3:31][O:30][C:29]1[CH:28]=[C:27]([CH:36]=[CH:35][C:32]=1[O:33][CH3:34])[CH2:26][CH2:25][N:24]([CH3:23])[CH2:2][CH2:3][CH2:4][C:5]1([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[S:10](=[O:11])[CH2:9][CH2:8][CH2:7][S:6]1=[O:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 77039N-MethylhomoveratrylamineHCID 22758376HCID 22758376, compound

Product 1

HCID 86734431HCID 86734431, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.65 g of 2-(3-chloropropyl)-2-(3,4-dimethoxyphenyl)-m-dithiane-1,3-dioxide, 7.8 g of N-methyl-homoveratrylamine and 20 ml of dimethyl sulphoxide are heated at 50° C under argon for 16 hours. The solution is then poured into 200 ml of water and made strongly alkaline. The excess N-methyl-homoveratrylamine is extracted with ether. The alkaline solution is then extracted with methylene chloride. The methylene chloride extracts are dried over magnesium sulphate. After evaporation of the solvent, the residue is taken up in acetone and treated with hydrogen chloride in dioxane (up to pH 2). The crystalline residue is recrystallized from acetone/acetonitrile and there is obtained N-(3,4-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propylamine-1,3-dioxide hydrochloride of melting point 148°-149° C (diastereomeric mixture).

Workup

  1. extractionThe excess N-methyl-homoveratrylamine is extracted with ether
  2. extractionThe alkaline solution is then extracted with methylene chloride
  3. dry with materialThe methylene chloride extracts are dried over magnesium sulphate
  4. customAfter evaporation of the solvent
  5. additiontreated with hydrogen chloride in dioxane (up to pH 2)
  6. customThe crystalline residue is recrystallized from acetone/acetonitrile

Sources & evidence

ORD record
ord-4302b8de35bb42878e0250257bedc680
Source dataset
uspto-grants-1978_02
Patent number
US04073797

Reaction notes

Loading…