Methanol → Methyl 1-aminocyclohexanoate

HRID 2184993Notes

Reaction equation

HRID 2184993 reaction equation
S(Cl)(Cl)=O.[NH2:5][C:6]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:15]O>>[NH2:5][C:6]1([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 13661-Aminocyclohexanecarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 4048819Methyl 1-aminocyclohexanoate

Procedure

51 ml of thionyl chloride were added in portions at −5° C. to 50 g (350 mmol) of 1-aminocyclohexane-1-carboxylic acid in 1.25 l of methanol. The reaction mixture was subsequently stirred at room temperature for 5 hours and allowed to stand overnight at room temperature. The methanol was removed in vacuo, the residue was mixed with water, and the aqueous solution was adjusted to pH 9 using saturated sodium carbonate solution and extracted twice with dichloromethane. The organic phase was dried over sodium sulfate and, after filtration, the solvent was removed in vacuo. Yield: 36.35 g (66%).

Workup

  1. waitto stand overnight at room temperature
  2. customThe methanol was removed in vacuo
  3. additionthe residue was mixed with water
  4. extractionextracted twice with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationafter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-16fd265e9a214205a90f9f1ebdad9552
Source dataset
uspto-grants-2002_06
Patent number
US06399643B1

Reaction notes

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