p-Toluenesulfonic acid → N-cyclopropylmethylphthalimide

HRID 1792911Notes

Reaction equation

HRID 1792911 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:12]1([CH2:15][N:16]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6811Phthalic AnhydrideHCID 75646Cyclopropanemethanamine

Product 1

HCID 4121050N-cyclopropylmethylphthalimide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

N-Cyclopropylmethylphthalimide is prepared as described in Example 2, starting with 4 g of phthalic anhydride, 2.3 cm3 of cyclopropylmethylamine and a catalytic amount of para-toluenesulfonic acid in 40 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 2 hours and is then cooled to a temperature in the region of 20° C. and stirred for 16 hours. The reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in dichloromethane and washed twice with saturated aqueous sodium bicarbonate solution. The organic phase is separated out after settling of the phases, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 4.3 g of N-cyclopropylmethylphthalimide are thus obtained in the form of a cottony white solid (Rf=0.46, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (40/60 by volume)).

Workup

  1. customN-Cyclopropylmethylphthalimide is prepared
  2. temperatureis then cooled to a temperature in the region of 20° C.
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  4. washwashed twice with saturated aqueous sodium bicarbonate solution
  5. customThe organic phase is separated out
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-f97ef69472944c5491d3545fbca46f8e
Source dataset
uspto-grants-2006_07
Patent number
US07078428B2

Reaction notes

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