3-Phenylpropylamine → HCID 18960800, compound

HRID 1084343Notes

Reaction equation

HRID 1084343 reaction equation
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[C:16]1([CH2:22][CH2:23][CH2:24][NH2:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:16]1([CH2:22][CH2:23][CH2:24][NH:25][C:2]2[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 162593-PhenylpropylamineHCID 14256374HCID 14256374, compound

Product 1

HCID 18960800HCID 18960800, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

500 mg of dimethyl 5-bromo-pyridine-2,4-dicarboxylate (from Example 3) are dissolved in 10 ml of toluene. 0.26 ml of phenylpropylamine are added dropwise and the mixture is stirred at 120° C. for 10 hours. After cooling, the solvent is evaporated off, the residue is taken up in ethyl acetate and the organic phase is washed with 2 portions each of citric acid, sodium bicarbonate solution and water. After drying over magnesium sulfate, the solvent is evaporated. Chromatography on silica gel gives 117 mg of product with a melting point of 102°-104° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off
  3. washthe organic phase is washed with 2 portions each of citric acid, sodium bicarbonate solution and water
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-fbaa2c34ed4b4b909a79f7eaf38cd28f
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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