Methanol → Methyl 1-aminocyclohexane-1-carboxylate hydrochloride
Reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[CH3:15][O:9][C:8]([C:2]1([NH2:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:10]Participants
4
Procedure
1-Amino-cyclohexanecarboxylic acid (49 g, 342 mmol) was added to a solution, cooled to 0° C., of thionyl chloride (49.6 ml, 684 mmol) in methanol (750 ml). The reaction mixture was stirred for 4 h under reflux and then overnight at room temperature. Then the mixture was heated again for 3 h under reflux and stirred overnight again at room temperature. The reaction solution was concentrated and the thionyl chloride residues were removed by dragging out with methanol and diethyl ether.
Workup
- temperatureunder reflux
- customovernight
- customat room temperature
- temperatureThen the mixture was heated again for 3 h
- temperatureunder reflux
- stirringstirred overnight again at room temperature
- concentrationThe reaction solution was concentrated
- customthe thionyl chloride residues were removed
Sources & evidence
- ORD record
- ord-d2ccf9972cc94a219c80c52d13fab8ee
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119633B2
Reaction notes
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