Homoveratrylamine → 1-{[2-(3,4-Dimethoxyphenyl)ethyl]amino}-3-[4-(diphenylmethyl)piperazin-1-yl]propan-2-ol

HRID 274906Notes

Reaction equation

HRID 274906 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[O:17][CH2:16]3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][CH2:35][NH2:36])[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:34][CH2:35][NH:36][CH2:16][CH:15]([OH:17])[CH2:14][N:11]2[CH2:12][CH2:13][N:8]([CH:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:9][CH2:10]2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 11430Potassium CarbonateHCID 102447781-(Diphenylmethyl)-4-[(oxiran-2-yl)methyl]piperazine

Product 1

HCID 30727001-{[2-(3,4-Dimethoxyphenyl)ethyl]amino}-3-[4-(diphenylmethyl)piperazin-1-yl]propan-2-olYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.08 g (0.01 mol) of 1-(diphenylmethyl)-4-(2,3-epoxypropyl)piperazine and 2 g (0.01 mol) of 2-(3,4-dimethoxyphenyl)ethylamine were refluxed with heating together with 200 ml of DMF for 24 hours in the presence of a catalytic amount of an alkali such as potassium carbonate. DMF was distilled off under reduced pressure, and a residue was extracted with ethyl acetate, and after washing with water and drying, the ethyl acetate was distilled off under reduced pressure to obtain 5.1 g of a crude subject compound of a viscous liquid. The obtained compound was refined by flush chromatography and fractional thin-layer chromatography with solvent mixtures of ethyl acetate--methanol and methylene chloride--methanol respectively to obtain 1.2 g of the subject compound in a viscous liquid state.

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. extractiona residue was extracted with ethyl acetate
  3. washafter washing with water
  4. customdrying
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customto obtain 5.1 g of a crude
  7. customby flush chromatography and fractional thin-layer chromatography with solvent mixtures of ethyl acetate

Sources & evidence

ORD record
ord-77b79991366c412498b2fb7374b56fc8
Source dataset
uspto-grants-1995_02
Patent number
US05391552

Reaction notes

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