Homoveratrylamine → HCID 13302060, compound

HRID 1285578Notes

Reaction equation

HRID 1285578 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[CH:17]=[CH:16][C:10]([O:11][CH:12]2[O:15][CH:13]2[CH3:14])=[CH:9][CH:8]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:23][CH2:24][NH2:25]>C(O)(C)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH2:23][CH2:24][NH:25][CH2:14][CH:13]([OH:15])[CH2:12][O:11][C:10]2[CH:16]=[CH:17][C:7]([C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=3)=[CH:8][CH:9]=2)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 20249502HCID 20249502, compound

Product 1

HCID 13302060HCID 13302060, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Compound 7 was dissolved in isopropanol (45 ml) and a solution of 3,4-dimethoxyphenethylamine (4.5 g., 0.025 ml.) was added dropwise. After the addition the solution was heated with stirring at 70° C. After 18 hours, the solution was concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with CHCl3 saturated with NH3. The product was crystallized from HCl/EtOH and recrystallized from isopropanol to yield 2.7 g. of 8, mp 192°-194° C.; 'H NMR (DMSO-6) 3.05 (6H, m), 3.7 (6H, d), 3.85 (3H, s), 4.3 (3H, m), 6.8 (3H, m), 7.2 (2H, d), 7.8 (4H, m).

Workup

  1. additionAfter the addition the solution
  2. temperaturewas heated
  3. concentrationthe solution was concentrated to dryness
  4. customThe residue was chromatographed on silica gel
  5. washthe product eluted with CHCl3 saturated with NH3
  6. customThe product was crystallized from HCl/EtOH
  7. customrecrystallized from isopropanol
  8. customto yield 2.7 g

Sources & evidence

ORD record
ord-9a66635809dc407d8ca74fe2fcd03a54
Source dataset
uspto-grants-1986_01
Patent number
US04567276

Reaction notes

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