Benzocaine → HCID 68697948, compound

HRID 2235158Notes

Reaction equation

HRID 2235158 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](O)=[O:19])[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH2:54]([O:56][C:57](=[O:65])[C:58]1[CH:63]=[CH:62][C:61]([NH2:64])=[CH:60][CH:59]=1)[CH3:55]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](=[O:19])[NH:64][C:61]3[CH:62]=[CH:63][C:58]([C:57]([O:56][CH2:54][CH3:55])=[O:65])=[CH:59][CH:60]=3)[CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68699381HCID 68699381, compound

Product 1

HCID 68697948HCID 68697948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-tert-butyl ester (1.0 g, 3.61 mmol) in dimethylformamide (20 ml) was treated with diisopropyl ethyl amine (0.51 g, 3.97 mmol, 1.1 equiv.), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluoro-phosphate (1.27 g, 3.97 mmol, 1.1 equiv.) and 4-amino-benzoic acid ethyl ester (0.65 g, 3.97 mmol, 1.1 equiv.). The mixture was stirred at room temperature overnight, then the solvent was evaporated and the residue purified by flash chromatography (heptane/ethyl acetate gradient) to afford 7-(4-ethoxycarbonyl-phenylcarbamoyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as a white solid, 1.1 g (70%). MS (ISP): m/e=423.1 (M−H).

Workup

  1. customthe solvent was evaporated
  2. customthe residue purified by flash chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-044b0e929b9c4e998d2cac80eafd03b1
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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