Diethylamine → Methyl 3-(2-ethoxycarbonylvinyl)-5-(3,4,5-trifluorophenyl)piperazine-1-carboxylate

HRID 554006Notes

Reaction equation

HRID 554006 reaction equation
C(NCC)C.[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH:14]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)[N:13](C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH:12]([CH:42]=[CH:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:11]1)=[O:9]>C(#N)C>[CH2:47]([O:46][C:44]([CH:43]=[CH:42][CH:12]1[NH:13][CH:14]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[C:18]([F:24])[CH:17]=2)[CH2:15][N:10]([C:8]([O:7][CH3:6])=[O:9])[CH2:11]1)=[O:45])[CH3:48]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 674607682-(2-ethoxycarbonylvinyl)-6-(3,4,5-trifluorophenyl)piperazine-1,4-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 4-methyl ester

Product 1

HCID 67464101Methyl 3-(2-ethoxycarbonylvinyl)-5-(3,4,5-trifluorophenyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diethylamine (2 mL) was added to a solution of 2-(2-ethoxycarbonylvinyl)-6-(3,4,5-trifluorophenyl)piperazine-1,4-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 4-methyl ester (1.03 g) in acetonitrile (10 mL), and the reaction solution was stirred at room temperature for one hour. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (heptane->ethyl acetate) to obtain 422 mg of an E/Z isomer mixture of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by silica gel column chromatography (heptane->ethyl acetate)
  3. customto obtain

Sources & evidence

ORD record
ord-0fe97f69f1be4f8493f5484152280e3d
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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