Triethylamine → N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate hyrochloride

HRID 596233Notes

Reaction equation

HRID 596233 reaction equation
[CH:1]1([NH:7][CH:8](O)[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:23]([Cl:25])=[O:24].C(OCC)(=[O:35])C>>[CH3:9][CH2:8][N:7]([C:21]1[C:20]([O:19][CH3:18])=[C:28]([O:29][CH3:30])[C:27]([O:31][CH3:32])=[CH:26][C:22]=1[C:23]([O-:35])=[O:24])[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:25]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 20285879Cyclohexylamino ethanol

Product 1

HCID 86734520N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate hyrochloride

Procedure

2.86 g. of cyclohexylamino ethanol and 2.02 g. of triethyl amine are dissolved in 30 ml. of anhydrous ethyl acetate. A solution of 4.6 g. of 3,4,5-trimethoxybenzoyl-chloride and 20 ml. of anhydrous ethyl acetate are added under stirring and boiling. The reaction mixture is refluxed for 2 hours, whereafter it is cooled and the precipitate is filtered off by suction and washed with ethyl acetate. The ethyl acetate solution is saturated with gaseous hydrochloric acid. The mixture is refluxed for an hour. On cooling white crystals precipitate. Thus N-2-ethyl-cyclohexylamino-3,4,5-trimethoxy-benzoate-hyrochloride is obtained. M.p.: 209° - 210° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours, whereafter it
  2. temperatureis cooled
  3. filtrationthe precipitate is filtered off by suction
  4. washwashed with ethyl acetate
  5. temperatureThe mixture is refluxed for an hour
  6. temperatureOn cooling white crystals precipitate

Sources & evidence

ORD record
ord-eb1b2547ed2e407689cd187d69bedb1f
Source dataset
uspto-grants-1977_03
Patent number
US04010193

Reaction notes

Loading…