Homoveratrylamine → HCID 9246104, compound

HRID 2238357Notes

Reaction equation

HRID 2238357 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.BrC1C=CC(CC(Cl)=O)=CC=1.[OH-].[Na+].[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[CH2:36][CH2:37][NH2:38]>C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:38][CH2:37][CH2:36][C:35]2[CH:39]=[CH:40][C:41]([O:42][CH3:43])=[C:33]([O:32][CH3:31])[CH:34]=2)=[O:11])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 181552Benzeneacetyl chloride, 4-bromo-

Product 1

HCID 9246104HCID 9246104, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent3×

Procedure

The intermediate 2-(4-bromo-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide (31) was prepared as follows: A solution of 4-bromo-phenylacetic acid (10.06 g, 46.8 mmol) and oxalyl chloride (101.9 g, 0.8 mol) in 400 mL of benzene was refluxed for 6 h. The solution was evaporated with benzene 3 times and dried in vacuum. A solution of 4-bromo-phenylacetic acid chloride (1.1 mol. equiv.) in CH2Cl2 was added to a mixture of 300 mL of 1N NaOH and solution of 3,4-di-methoxy-phenethylamine (6.55 g, 36.1 mmol) in 300 mL of CH2Cl2. The reaction mixture was stirred overnight at room temperature. Another portion of acid chloride (0.1 eq.) in 20 mL of CH2Cl2 was added and stirred for 1 h. Organic phase was separated, washed with 1N HCl, 1N NaOH, water, dried over Na2SO4, filtered and evaporated. A residue was crystallized from EtOAc-hexanes mixture. Yield is 11.54 g (84.5%).

Workup

  1. customThe solution was evaporated with benzene 3 times
  2. customdried in vacuum
  3. stirringstirred for 1 h
  4. customOrganic phase was separated
  5. washwashed with 1N HCl, 1N NaOH, water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customA residue was crystallized from EtOAc-hexanes mixture

Sources & evidence

ORD record
ord-1ee9d86af72e464084dfbfed8fbc4805
Source dataset
uspto-grants-2010_05
Patent number
US07718672B2

Reaction notes

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