Diethylamine → 2-[(Diethylamino)carbonyl]cyclohexanecarboxylic acid

HRID 2284824Notes

Reaction equation

HRID 2284824 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C@@H:6]12[C:15](=[O:16])[O:14][C:12](=[O:13])[C@@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2>C.[Cl-].[Cl-]>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12]([CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[C:15]([OH:14])=[O:16])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 35545372-[(Diethylamino)carbonyl]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 20976018Dichloride methaneSolvent

Procedure

Model compound synthesis and hydrolytic kinetics measurement (Scheme 4—FIG. 4): Briefly, N,N-diethylamine (415 μL, 4 mmol) and 1,2-cis-cyclohexanedicarboxylic anhydride (617 mg, 4 mmol) were dissolved in 10 mL dichloride methane. The reaction was kept at room temperature for 2 h with stirring. The solvent was then removed by rotary evaporation to obtain the raw product. The raw product was purified by recrystallizing from benzene to get 2-[(diethylamino)carbonyl]cyclohexanecarboxylic acid. 1H NMR (400 MHz, CDCl3): δ (ppm): 3.60-3.22 (m), 2.77 (m), 2.51-2.45 (m), 1.87-1.66 (m), 1.58-1.46 (m), 1.49-1.39 (m), 1.28 (q), 1.17 (t). Similarly, 2-[(isopropylamino)carbonyl]cyclohexanecarboxylic acid was synthesized. 1H NMR (400 MHz, CDCl3): δ (ppm): 3.83 (q), 2.73 (q), 2.64 (q), 1.87 (m), 1.79 (m), 1.64 (m), 1.45 (m), 1.33 (m), 1.01 (d).

Workup

  1. customModel compound synthesis and hydrolytic kinetics measurement (Scheme 4—FIG. 4)
  2. customThe solvent was then removed by rotary evaporation
  3. customto obtain the raw product
  4. customThe raw product was purified
  5. customby recrystallizing from benzene

Sources & evidence

ORD record
ord-a08e7e3dc86148599252057b99e0e6c4
Source dataset
uspto-grants-2015_09
Patent number
US09145472B2

Reaction notes

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