Thionyl Chloride → Methyl 4-aminocyclohexanecarboxylate

HRID 2167768Notes

Reaction equation

HRID 2167768 reaction equation
S(Cl)(Cl)=O.[NH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1.[C:15](=O)(O)[O-].[Na+]>CO>[NH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1715604-Aminocyclohexanecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 422580Methyl 4-aminocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thionyl chloride (4.15 g, 34.92) was added to a cold (0° C.) stirred solution of 4-aminocyclohexane carboxylic acid (1 g, 6.98 mmol) in MeOH (10 mL). The reaction mixture was stirred under reflux conditions for 12-16 h. The reaction mixture was then concentrated under reduced pressure. The residue obtained was diluted with ice cold water, basified with aqueous sodium bicarbonate solution and extracted with DCM. The DCM layer was washed with water followed by brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 650 mg of the title compound as a brown liquid. MS (ESI): m/z 158 (M+H)

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue obtained
  3. additionwas diluted with ice cold water
  4. extractionextracted with DCM
  5. washThe DCM layer was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b29df29fc7ff4b46a32d6fa333e81187
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

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