Ethanol → 1-Isopropylpiperidine-4-Carboxylic Acid
Reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1)[CH3:3].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(O)C.C(=O)([O-])[O-].[NH4+].[NH4+]>O>[CH3:3][CH:2]([N:4]1[CH2:5][CH2:6][CH:7]([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]1)[CH3:1]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
Ethyl 1-(1-methylethyl)-4-piperidine carboxylate (3.6 g, 18 mmol, 1 eq) was combined with barium hydroxide octahydrate (10.4 g, 33 mmol, 1.8 eq) in a mixture of 70 mL of water with 44 mL of ethanol. The mixture was heated at 60° C. for 1.3 h. The reaction mixture was concentrated in vacuo and diluted with 70 mL of water. Ammonium carbonate (6.9 g, 87 mmol, 4.8 eq) was added portionwise and the reaction mixture was stirred at rt overnight. The mixture was filtered through diatomaceous earth, concentrated, and lyophilized to provide 3.1 g (100%) of 1-(1-methylethyl)-4-piperidine carboxylic acid as a white solid.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additiondiluted with 70 mL of water
- filtrationThe mixture was filtered through diatomaceous earth
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-476bf030143d4cc5972e06c00e6785ce
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06534531B2
Reaction notes
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