Homoveratrylamine → SB-237376

HRID 1601340Notes

Reaction equation

HRID 1601340 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.[CH2:17]([NH2:29])[CH2:18][C:19]1[CH:28]=[CH:27][C:24]([O:25][CH3:26])=[C:21]([O:22][CH3:23])[CH:20]=1.C(N(CC)CC)C>C(Cl)Cl>[ClH:1].[CH3:23][O:22][C:21]1[CH:20]=[C:19]([CH2:18][CH2:17][NH:29][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:16])[C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[CH:28]=[CH:27][C:24]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 8421HomoveratrylamineHCID 8471TriethylamineHCID 3421653N-(3-chloropropyl)-4-nitrobenzamide

Product 1

HCID 9845213SB-237376Yield 23.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.62 g (44 mmol) N-(3-chloropropyl)-4-nitrobenzamide (D3), 8.1 g (45 mmol) homoveratrylamine and 6.26 ml triethylamine in 200 ml methylene chloride was refluxed for 48 h. The solvent was then concentrated in vacuo and the residue dissolved in water. The aqueous phase was first washed with methylene chloride, then made basic with aqueous NaOH and finally extracted twice with methylene chloride. This second organic phase was dried over MgSO4 and concentrated in vacuo affording 12 g of a crude residue. This residue was purified by chromatography on silicagel using CH2Cl2 /MeOH/NH4OH: 85/10/5 to afford 4.4 g of the title compound as an yellow oil (free base).

Workup

  1. concentrationThe solvent was then concentrated in vacuo
  2. dissolutionthe residue dissolved in water
  3. washThe aqueous phase was first washed with methylene chloride
  4. extractionfinally extracted twice with methylene chloride
  5. dry with materialThis second organic phase was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customaffording 12 g of a crude residue
  8. customThis residue was purified by chromatography on silicagel

Sources & evidence

ORD record
ord-23ba9b4686454633b0a023f2fe66b624
Source dataset
uspto-grants-1999_11
Patent number
US05977179

Reaction notes

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