Acetic Acid → HCID 66664954, compound

HRID 1773534Notes

Reaction equation

HRID 1773534 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:25])[CH2:11][C:12]1[CH:17]=[C:16](Cl)[C:15]([N+:19]([O-])=O)=[CH:14][C:13]=1[N+:22]([O-])=O)[CH3:8].C(O)(=O)C>ClCCl.[Zn]>[CH2:7]([O:9][C:10](=[O:25])[CH2:11][C:12]1[CH:17]=[C:16]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:15]([NH2:19])=[CH:14][C:13]=1[NH2:22])[CH3:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 86661369HCID 86661369, compound

Product 1

HCID 66664954HCID 66664954, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

Piperidine (120 mg) was added to a solution of (5-chloro-2,4-dinitro-phenyl)-acetic acid ethyl ester (150 mg) in dichloromethane (5 mL) and the resulting mixture was stirred at room temperature for 10 minutes. Glacial acetic acid (0.3 mL) and zinc dust (1 scoop) were added and the reaction mixture was stirred at room temperature for 20 minutes. The resulting mixture was filtered through a CELITE™ pad, the filter cake was washed with dichloromethane and the filtrate was evaporated under reduced pressure. The residue was then diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give (2,4-diamino-5-piperidin-1-yl-phenyl)-acetic acid ethyl ester. This material was dissolved in toluene (2.5 mL) and heated at 150° C. in a microwave reactor for 10 minutes. The reaction mixture was then cooled, evaporated under reduced pressure and the residue was purified by flash chromatography (DCM/MeOH, 95/5) to give 30 mg of 6-amino-5-piperidin-1-yl-1,3-dihydro-indol-2-one. MS=232 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 20 minutes
  2. filtrationThe resulting mixture was filtered through a CELITE™ pad
  3. washthe filter cake was washed with dichloromethane
  4. customthe filtrate was evaporated under reduced pressure
  5. additionThe residue was then diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-65edeb0f3bfe4940862284617d4401bc
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…