Benzocaine → HCID 70496554, compound

HRID 2408035Notes

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].[CH3:13][S:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)(=[O:16])=[O:15].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:20]([C:19]1[CH:22]=[CH:23][CH:24]=[C:17]([S:14]([CH3:13])(=[O:16])=[O:15])[CH:18]=1)[CH2:51][C:52]2([CH3:54])[CH3:53])=[O:12])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-aminobenzoic acid ethyl ester (3.3 g, 20 mmol), 3-methanesulfonyl benzaldehyde (3.68 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 2-(3-methanesulfonyl-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (3.3 g, 43%) as a white solid: MS (ESI) M+1=388.3.

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-30ae4b92a0bb4693abd615872e4f8ead
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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