1-Iodopropane → HCID 69129839, compound

HRID 478641Notes

Reaction equation

HRID 478641 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(C(C)C)[CH:20]([CH3:22])[CH3:21])C.ICCC>COCCOC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:21][CH2:20][CH3:22])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 336431-IodopropaneHCID 81531DiisopropylethylamineHCID 24904226Methyl 4-(piperidin-4-yl)benzoate

Product 1

HCID 69129839HCID 69129839, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

4-Piperidin-4-yl-benzoic acid methyl ester (28 mmol), ethyldiisopropylamine (31 mol) and 1-iodopropane (42 mmol) are dissolved in 1,2-dimethoxyethane (100 ml) and the mixture is heated at 70° C. overnight. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH=9:1 as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale brown powder with Rf=0.35 (CH2Cl2/MeOH=9:1) is obtained.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (to ensure basic conditions)
  3. extractionextracted three times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel with CH2Cl2/MeOH=9:1 as mobile phase
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationthe solid filtered of and
  11. customdried (vacuum)
  12. customA pale brown powder with Rf=0.35 (CH2Cl2/MeOH=9:1) is obtained

Sources & evidence

ORD record
ord-721fcd3d612a4e6daf66e05989905e19
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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