Citric Acid → HCID 22330196, compound

HRID 347720Notes

Reaction equation

HRID 347720 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N+:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:12]([O-:14])=[O:13])[CH:20]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 16773-Nitrophenylboronic AcidHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 22330196HCID 22330196, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-piperidinecarboxylic acid ethyl ester (25.0 g) and 3-nitrophenylboronic acid (31.9 g) in dichloromethane (1.0 L) are added pyridine (64.8 ml), anhydrous copper (II) acetate (28.9 g) and Molecular Sieves 4 Å (500 g), and the mixture was stirred at 25° C. for 3 days. The reaction solution is poured into 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with aqueous sodium hydrogen carbonate solution and saturated brine, and the solvent is evaporated under reduced pressure to give the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with aqueous sodium hydrogen carbonate solution and saturated brine
  3. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-61e1ca263ca84ad785ffa29e8332fc3b
Source dataset
uspto-grants-2007_02
Patent number
US07176199B2

Reaction notes

Loading…