6-Aminohexanoic Acid → 6-(cis-1,2,3,6-Tetrahydrophthalimido)hexanoic acid

HRID 35797

Reaction equation

HRID 35797 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C@H:3]2[CH2:7][CH:8]=[CH:9][CH2:10][C@@H:2]12.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]>C(O)(=O)C>[C:4]1(=[O:6])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:1](=[O:11])[C@H:2]2[CH2:10][CH:9]=[CH:8][CH2:7][C@@H:3]12

Participants

4

Reactant 2

HCID 5646-Aminohexanoic AcidHCID 98495Tetrahydrophthalic anhydride, cis-

Product 1

HCID 15516686-(cis-1,2,3,6-Tetrahydrophthalimido)hexanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
4 °C

Procedure

31 g (0.2 mole) of cis-1,2,3,6-tetrahydrophthalic anhydride and 26.2 g (0.2 mole) of 6-aminohexanoic acid are dissolved in 400 ml. of acetic acid and warmed 3 hours on a steam bath. The cooled solution is concentrated to remove most of the acetic acid and the residue taken up in 200 ml. of methylene chloride. The solution is washed twice with water and dried over sodium sulfate. The solvent is removed and the residue taken up in 500 ml toluene. Para-toluenesulfonic acid (1 g) is added to the solution, followed by reflux for 10 hrs. with a Dean-Stark water trap. The solution is cooled and concentrated to about 50 ml and diluted with 50 ml of hexane. The mixture is shaken for a few minutes until the oil crystallizes then cooled at 4° C. for several hours, filtered and dried at 50° C. The light yellow crystals (32 g) are taken up in chloroform and filtered to remove any precipitate. The solution is diluted with hexane near the cloud point, cooled until a crystalline mass accumulates, filtered and dried to yield white crystals, m.p. 85°-87° C.

Workup

  1. concentrationThe cooled solution is concentrated
  2. customto remove most of the acetic acid
  3. washThe solution is washed twice with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed
  6. additionPara-toluenesulfonic acid (1 g) is added to the solution
  7. temperatureby reflux for 10 hrs
  8. temperatureThe solution is cooled
  9. concentrationconcentrated to about 50 ml
  10. additiondiluted with 50 ml of hexane
  11. customcrystallizes
  12. filtrationfiltered
  13. customdried at 50° C
  14. filtrationfiltered
  15. customto remove any precipitate
  16. additionThe solution is diluted with hexane near the cloud point
  17. temperaturecooled until a crystalline mass accumulates
  18. filtrationfiltered
  19. customdried
  20. customto yield white crystals, m.p. 85°-87° C.

Sources & evidence

ORD record
ord-8ae8e440dc58469e85ec63cb2158cff9
Source dataset
uspto-grants-1995_05
Patent number
US05411869

Linked notes

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