Methanol → HCID 178501212, compound

HRID 1896308Notes

Reaction equation

HRID 1896308 reaction equation
S(Cl)(Cl)=O.[CH2:5]([NH:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=[O:20])[CH2:15][CH2:14]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:22]O>>[CH2:5]([NH:12][C@@H:13]1[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178525768HCID 178525768, compound

Product 1

HCID 178501212HCID 178501212, compoundYield 66%

Procedure

Thionyl chloride was added to a solution of compound cis-4-(benzylamino)cyclohexanecarboxylic acid (0.5 g, 2.1 mmol) in MeOH (7 ml) at 0° C. and the reaction mixture was heated at reflux for 18 h. Then volatiles were removed in vacuo and the reaction mixture was basified using saturated sodium bicarbonate. The aqueous layer was extracted with ethyl acetate, water and brine solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 350 mg of cis-methyl 4-(benzylamino)cyclohexanecarboxylate (66%) as brown color solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customThen volatiles were removed in vacuo
  4. extractionThe aqueous layer was extracted with ethyl acetate, water and brine solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f7764591bdd54740b54d6026c4b91ff4
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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