Benzocaine → HCID 70496998, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:2].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH2:51]=[C:52]([CH3:54])[CH3:53]>C(#N)C>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][CH:6]=1)[NH:11][CH:18]([C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([C:14]([F:24])([F:23])[F:13])[CH:16]=1)[CH2:51][C:52]2([CH3:54])[CH3:53])=[O:12])[CH3:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), 3-trifluoromethyl benzaldehyde (3.48 g, 20 mmol) and ytterbium(III) triflate hydrate (1.86 g, 3 mmol) in acetonitrile (150 mL) was cooled to 0° C. in a sealed reaction bottle. Then a cooled solution of isobutene (5.6 g, 100 mmol) was added into. The reaction mixture was heated to 90° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) to afford 4,4-dimethyl-2-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.0 g, 40%) as a white solid: MS (ESI) M+1=378.3.
Workup
- temperatureThe reaction mixture was heated to 90° C.
- customThe solvent was removed in vacuo
- customthe residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-c10db924be1a4ae7a857c9ee7e42404c
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809369B2
Reaction notes
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