Methanol → Methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[C:18]([CH2:27][CH3:28])=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=3)[C:22]([OH:24])=[O:23])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH3:34]O>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([C:17]3[C:18]([CH2:27][CH3:28])=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=3)[C:22]([O:24][CH3:34])=[O:23])=[O:16])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1)#[N:2]Participants
4
Procedure
To a round-bottom flask was added a solution of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoic acid (compound 211.6, 600 mg, 1.59 mmol, 1.00 equiv) in methanol (30 mL). To this was added sulfuric acid (500 mg, 5.10 mmol, 3.20 equiv) dropwise. The resulting solution was stiffed for 15 h at 60° C. After cooling to ambient temperature, the mixture was concentrated in vacuo. The residue was diluted with 20 mL of H2O. The aqueous phase was extracted with 3×20 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. This resulted in 500 mg (80%) of methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoate as a yellow oil.
Workup
- concentrationthe mixture was concentrated in vacuo
- additionThe residue was diluted with 20 mL of H2O
- extractionThe aqueous phase was extracted with 3×20 mL of ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customThis resulted in 500 mg (80%) of methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-4-ethyl-2-methylbenzoate as a yellow oil
Sources & evidence
- ORD record
- ord-5384dd52d8a94e7f8539bf35dd4b8aad
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871790B2
Reaction notes
Loading…