Benzenepropanal → 5-Bromo-1,2,3,4-tetrahydro-7-nitro-2-(3-phenylpropyl)-8-isoquinolinamine

HRID 1106430Notes

Reaction equation

HRID 1106430 reaction equation
Cl.[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.[CH:17](=O)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([BH3-])#N.[Na+]>CO.O>[Br:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([NH2:16])=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:8]2

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 5003444Sodium cyanoborohydrideHCID 21253084HCID 21253084, compound

Product 1

HCID 155241945-Bromo-1,2,3,4-tetrahydro-7-nitro-2-(3-phenylpropyl)-8-isoquinolinamineYield 94%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of the product from Example 5 (1 g, 3.24 mmol) and hydrocinnamaldehyde (0.94 g, 7 mmol) in 2:1 MeOH/H2O (50 mL) was treated with sodium cyanoborohydride (0.56 g, 9 mmol) portionwise under nitrogen and stirred for six hours. The solvent was decanted and the semi-solid was dissolved in dichloromethane, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude compound was chromatographed on silica gel (eluted with 25% ethyl acetate in hexane) to give the title compound (1.18 g, 94% yield) as a brown oil.

Workup

  1. customThe solvent was decanted
  2. dissolutionthe semi-solid was dissolved in dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude compound was chromatographed on silica gel (eluted with 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-824cb4e271904b11af7b730098fe31ee
Source dataset
uspto-grants-2000_05
Patent number
US06057313

Reaction notes

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