Hydrochloric Acid → (1-Cyclohexylcarbamoylmethyl-cyclohexyl)-acetic acid

HRID 455902Notes

Reaction equation

HRID 455902 reaction equation
[C:1]12([CH2:12][C:11](=[O:13])[O:10][C:8](=[O:9])[CH2:7]1)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>ClCCl.O>[CH:14]1([NH:20][C:11]([CH2:12][C:1]2([CH2:7][C:8]([OH:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7965CyclohexylamineHCID 27342891,1-Cyclohexanediacetic Anhydride

Product 1

HCID 43235048(1-Cyclohexylcarbamoylmethyl-cyclohexyl)-acetic acidYield 115.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-cyclohexanediacetic anhydride (0.911 g, 5.0 mmol) and cyclohexylamine (0.63 mL, 5.5 mmol) in dichloromethane (10.0 mL) was stirred overnight at room temperature. The reaction mixture was diluted with H2O (5 mL) and the aqueous layer was acidified to pH-5 using 6 N HCl. The organic layer was collected. The aqueous layer was extracted with additional dichloromethane (5 mL). The organic extracts were combined, dried with sodium sulfate, filtered and concentrated to dryness to give crude title compound (1.63 g, 95% purity). (m/z): [M+H]+ calcd for C16H27NO3, 282.21. Found 282.5.

Workup

  1. customThe organic layer was collected
  2. extractionThe aqueous layer was extracted with additional dichloromethane (5 mL)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7ac9be8c538f42b0b9e09dfeb77da495
Source dataset
uspto-grants-2013_07
Patent number
US08497287B2

Reaction notes

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