Homoveratrylamine → HCID 20130080, compound

HRID 845720Notes

Reaction equation

HRID 845720 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].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.Cl[C:31]([O:33][CH:34]([Cl:36])[CH3:35])=[O:32]>C(Cl)(Cl)Cl>[Cl:36][CH:34]([O:33][C:31]([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:32])[CH3:35]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 20130080HCID 20130080, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.8 g of 3,4-dimethoxyphenethylamine in 50 ml of chloroform 2.2 g of proton sponge® was added. The reaction mixture was cooled in an ice bath. To the ice-cold solution was added with stirring 1.4 g of 1-chloroethyl chloroformate. The cooling bath was removed and the reaction mixture was kept stirred at room temperature for 72 hours. It was then washed with water, 3N HCl and water. After drying over sodium sulfate, the chloroform solution was evaporated to a thick oil weighing 2.1 g. NMR (CDCl3) δ1.75 (3H, d, J=7 Hz, CH3CH), 2.78 (2H, t, J=6 Hz, ArCH2), 3.4 (2H, broad t, NHCH2), 3.9 (6H, s, OMe), 4.9 (1H, broad NH) and 6.4-6.85 (CHCl and aromatic). IR (film) ν3350, 1722, 1512, 1260, 1240, 1138 cm-1.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customThe cooling bath was removed
  3. washIt was then washed with water, 3N HCl and water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe chloroform solution was evaporated to a thick oil

Sources & evidence

ORD record
ord-05e5b4327cfc4f048b4874fcab24020f
Source dataset
uspto-grants-1988_07
Patent number
US04760057

Reaction notes

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