Homoveratrylamine → HCID 58906470, compound

HRID 1295420Notes

Reaction equation

HRID 1295420 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[OH-].[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[CH2:25][CH2:26][NH2:27]>C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:27][CH2:26][CH2:25][C:24]2[CH:28]=[CH:29][C:30]([O:31][CH3:32])=[C:22]([O:21][CH3:20])[CH:23]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8421HomoveratrylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 74653(3-Bromophenyl)acetic acid2×

Product 1

HCID 58906470HCID 58906470, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent3×

Procedure

2-(3-Bromo-phenyl)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide (41) was prepared as follows: A solution of 3-bromo-phenylacetic acid (2.0 g, 9.3 mmol) and oxalyl chloride (36.4 g, 0.287 mol) in 80 mL of benzene was refluxed for 6 h. The solution was evaporated with benzene 3 times and dried in vacuum. A solution of 3-bromo-phenylacetic acid (1.1 eq.) in CH2Cl2 was added to mixture of 100 mL of 1N NaOH and solution of 3,4-di-methoxy-phenethylamine (1.31 g, 7.22 mmol) in 100 mL of CH2Cl2. The reaction mixture was stirred overnight at r.t. Another portion of acid chloride (0.1 eq.) in 10 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 mixtures. Yield is 2.59 g (95%).

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 mixtures

Sources & evidence

ORD record
ord-ae7b17bfc94d4c67aab4583e50046e96
Source dataset
uspto-grants-2007_07
Patent number
US07241774B2

Reaction notes

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