Morpholine → 2-(Morpholine-4-carbonyl)cyclohexane-1-carboxylic acid

HRID 427392Notes

Reaction equation

HRID 427392 reaction equation
[C@@H:1]12[C:10](=[O:11])[O:9][C:7](=[O:8])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C(Cl)Cl>[N:12]1([C:7]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]2[C:10]([OH:9])=[O:11])=[O:8])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 31145632-(Morpholine-4-carbonyl)cyclohexane-1-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-1,2-cyclohexane dicarboxylic anhydride (1.0 g, 6.49 mmol) in CH2Cl2 (16 mL) was added morpholine (0.56 g, 6.49 mmol) at 0° C., the resulting mixture was allowed to stir at room temperature overnight (20 h). When complete the reaction mixture was washed with HCl (1.0 N, 20 mL) then with H2O (2×20 mL). The combined aqueous layers were extracted with CH2Cl2 (3×10 mL), and the combined organic layers were dried over MgSO4, the solvent was evaporated in vacuo to give the title compound (1.4 g, 90%/) as a white solid which was used later without further purification.

Workup

  1. washWhen complete the reaction mixture was washed with HCl (1.0 N, 20 mL)
  2. extractionThe combined aqueous layers were extracted with CH2Cl2 (3×10 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-ddbeeefd8af747ce8d0a080bcde97eae
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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