Diclofenac → HCID 178458017, compound

HRID 1360003Notes

Reaction equation

HRID 1360003 reaction equation
C([N:5]([CH2:9][CH:10](N)[CH3:11])[C:6](=[O:8])[OH:7])(C)(C)C.[CH:13]1[CH:14]=[CH:15][C:16]([NH:23][C:24]2[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=2[Cl:30])=[C:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:18]=1.CCN=C=NCCCN(C)C.Cl.C(OCC)(=O)C>ClCCl.CN(C1C=CN=CC=1)C>[C:6]([N-:5][CH2:9][CH2:10][CH3:11])([O:7][C:17]([CH3:19])([CH3:18])[CH3:16])=[O:8].[CH:13]1[CH:14]=[CH:15][C:16]([NH:23][C:24]2[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:31])=[C:17]([CH2:19][C:20]([OH:22])=[O:21])[CH:18]=1

Participants

7

Reactant 4

HCID 3033DiclofenacHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71650669HCID 71650669, compound

Product 1

HCID 178458017HCID 178458017, compoundYield 157,164.297%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In 3 ml of dichloromethane, 338.4 mg (1.94 mmol) of tert-butyl N-(2-aminopropyl)carbamic acid (manufactured by Tokyo Kasei Kogyo) and 694.4 mg (2.34 mmol) of diclofenac were dissolved, and under ice-cooling, 59.0 mg (0.483 mmol) of DMAP and 505.3 mg (2.64 mmol) of WSCI.HCl were added thereto, followed by stirring for 70 minutes and then stirred at room temperature for 90 minutes. Ethyl acetate was added thereto, followed by separation by washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively. After dehydration with sodium sulfate, ethyl acetate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 835.5 g (95%) of the titled compound. The structure was identified by 1H-NMR.

Workup

  1. temperatureunder ice-cooling
  2. stirringstirred at room temperature for 90 minutes
  3. customfollowed by separation
  4. washby washing with 5% aqueous citric acid solution, 5% aqueous sodium hydrogen carbonate solution and saturated brine consecutively
  5. customAfter dehydration with sodium sulfate, ethyl acetate was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b8b0bbfc68c74bfb9213ac7e22e6ed50
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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