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

HRID 1879313Notes

Reaction equation

HRID 1879313 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-ad2f11f8c34048438faaecbbb7e3a147
Source dataset
uspto-grants-2012_11
Patent number
US08314128B2

Reaction notes

Loading…