Hydrochloric Acid → HCID 86661015, compound

HRID 1617625Notes

Reaction equation

HRID 1617625 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:15][C:16]([OH:18])=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl.[CH3:20][NH:21][O:22][CH3:23].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl>ClCCl.O>[CH3:23][O:22][N:21]([CH3:20])[C:16](=[O:18])[CH2:15][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 66666611HCID 66666611, compound

Product 1

HCID 86661015HCID 86661015, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [1-(4-methoxy-phenyl)-cyclohexyl]-acetic acid (1.2 g) in dichloromethane (9.7 ml) was added N,O-dimethylhydroxylamine hydrochloride (577 mg). The mixture was cooled in an ice bath. 1,1′-Carbonyldiimidazole (1.01 g) was added. The mixture was stirred for 5 min at 0° C. and for 2 days at room temperature. A mixture of water and 1 M HCl was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (20 g NH3-modified SiO2, cyclohexane/ethyl acetate 1:0 to 3:2) to give the title compound (1.13 g) as a colorless oil, MS (ESI+): m/z=292.2 [M+H]+.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe product was purified by chromatography (20 g NH3-modified SiO2, cyclohexane/ethyl acetate 1:0 to 3:2)

Sources & evidence

ORD record
ord-af0d2f629ce24556a7d0dbc3d9bcee42
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…