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

HRID 480230Notes

Reaction equation

HRID 480230 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 a 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-25dfe7b79b3e46b68b4ee5d840bd8094
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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