1,3-Propanedithiol → N-[3-(3,4-dimethoxyphenyl)propyl]-N-methylamine

HRID 1704798Notes

Reaction equation

HRID 1704798 reaction equation
[Cl:1]CCCCCC(C1C=CC(OC)=C(OC)C=1)=O.CNCCC1C=CC([O:29][CH3:30])=C(OC)C=1.[C:33]([OH:38])(=O)C(O)=O.CNCCCC1SCCCS1.C(S)CCS.CO[C:57]1[CH:58]=[C:59]([C:65](=[O:84])[CH2:66][CH2:67][CH2:68][N:69]([CH2:71][CH2:72][CH2:73][C:74]2[CH:79]=[CH:78][C:77]([O:80][CH3:81])=[C:76]([O:82][CH3:83])[CH:75]=2)C)[CH:60]=[CH:61][C:62]=1OC>CC(C)=O>[CH3:33][O:38][CH:67]([CH:68]([O:29][CH3:30])[Cl:1])[CH2:66][C:65]([C:59]1[CH:58]=[CH:57][CH:62]=[CH:61][CH:60]=1)=[O:84].[CH3:83][O:82][C:76]1[CH:75]=[C:74]([CH2:73][CH2:72][CH2:71][NH:69][CH3:68])[CH:79]=[CH:78][C:77]=1[O:80][CH3:81]

Participants

8

Reactant 5

HCID 80131,3-PropanedithiolHCID 77039N-MethylhomoveratrylamineHCID 227583446-Chloro-1-(3,4-dimethoxyphenyl)hexan-1-oneHCID 54470276HCID 54470276, compoundHCID 131711355HCID 131711355, compound

Product 2

HCID 7131256N-[3-(3,4-dimethoxyphenyl)propyl]-N-methylamineHCID 20509881HCID 20509881, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-chloro-3'4'-dimethoxyhexanophenone and N-methyl-homoveratrylamine. 2-(3,4-Dimethoxyphenyl)-N-[3,4-dimethoxyphenyl)-propyl]-N-methyl-m-dithiane-2-propylamine oxalate (1:1) of melting point 116°-118° C. (from acetone); starting from 1,3-propanedithiol and 3',4'-dimethoxy-4-[[(3,4-dimethoxyphenyl)-propyl]-methylamino]-butyrophenone, obtained from 3,4-dimethoxy-γ-chlorobutyrophenone and 3-(3,4-dimethoxyphenyl)-N-methylpropylamine.

Sources & evidence

ORD record
ord-e4cd4eae17284e96954a667cdd5b37f6
Source dataset
uspto-grants-1978_11
Patent number
US04127588

Reaction notes

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