Homoveratrylamine → HCID 21478970, compound

HRID 2292589Notes

Reaction equation

HRID 2292589 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][NH2:8].[C:14](=O)([O:23]C1C=CC([N+]([O-])=O)=CC=1)[O:15][C:16]([O:19][C:20](=[O:22])[CH3:21])([CH3:18])[CH3:17]>CN(C)C=O.O>[C:20]([O:19][C:16]([O:15][C:14]([NH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:23])([CH3:18])[CH3:17])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 8421HomoveratrylamineHCID 222720091-(Acetyloxy)-1-methylethyl 4-nitrophenyl carbonate

Product 1

HCID 21478970HCID 21478970, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-dimethoxyphenethylamine (110 mg) and acetoxyisopropyl p-nitrophenyl carbonate (0.18 g) in dimethylformamide (3 mL) was stirred at room temperature for 18 hours. The reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate. The ethyl acetate extract was washed with water, ice cold 1% aqueous sodium hydroxide, 1N HCl, water and brine. The organic extract was dried over sodium sulfate and evaporated. The residue (0.11 g) was purified by preparative thin layer chromatography on silica gel plates. The title compound (75 mg) was eluted with ethyl acetate-chloroform (5:95). 1H NMR (CDCl3) δ 1.81 (6H, s), 2.05 (3H, s), 2.75 (2H, t), 3.36 (2H, m), 4.85 (1H, br, t), 6.71-6.84 (3H, m); 13C NMR (CDCl3) δ 22.05, 25.9, 35.45, 41.91, 55.76, 55.83, 105.07, 111.29, 111.87, 120.61, 131.09, 147.59, 148.91, 153.36 and 168.79; 1R (film) 3370, 2941, 1748, 1718, 1517, 1464, 1370, 1261, 1238, 1140, 1027 cm-1 ; HRMS (e/m) calculated for C16H23NO6, 325.1525; found, 325.1512.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water, ice cold 1% aqueous sodium hydroxide, 1N HCl, water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. customevaporated
  7. customThe residue (0.11 g) was purified by preparative thin layer chromatography on silica gel plates
  8. washThe title compound (75 mg) was eluted with ethyl acetate-chloroform (5:95)

Sources & evidence

ORD record
ord-5b91d1e8457342389d05532b1d7648c1
Source dataset
uspto-grants-1997_11
Patent number
US05684018

Reaction notes

Loading…