Succinic anhydride → N-Cyclohexyl-succinamic acid

HRID 375100Notes

Reaction equation

HRID 375100 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH:8]1([NH2:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>N1C=CC=CC=1>[CH:8]1([NH:14][C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 7965Cyclohexylamine

Product 1

HCID 730603N-Cyclohexyl-succinamic acidYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Succinic anhydride (2.59 g, 25.9 retool) was dissolved in pyridine (15 ml). Cyclohexylamine was added dropwise to the solution at 0°. Thereafter, the mixture was stirred at room temperature (20°-22°) for 6 h. The pyridine was removed under reduced pressure. The residue was poured into 10% aqueous citric acid. The resulting precipitate was collected, washed thoroughly with 10% aqueous citric acid and then water. The precipitate was dried under vacuum to give the title compound (3.81 g, 74%), mp 168°-170°. The structure of the product was confirmed by NMR.

Workup

  1. customThe pyridine was removed under reduced pressure
  2. additionThe residue was poured into 10% aqueous citric acid
  3. customThe resulting precipitate was collected
  4. washwashed thoroughly with 10% aqueous citric acid
  5. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-436a15336f5b4116ab435d05a006039d
Source dataset
uspto-grants-1996_01
Patent number
US05484771

Reaction notes

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