Acetic Acid → 1-(1-Methyl(4-piperidyl))-6-nitroindoline

HRID 887572Notes

Reaction equation

HRID 887572 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:13][N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.CC(O)=O.C([O-])(O)=O.[Na+]>ClC(Cl)C>[CH3:13][N:14]1[CH2:19][CH2:18][CH:17]([N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=3)[CH2:8][CH2:9]2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 297576-NitroindolineHCID 740491-Methyl-4-piperidoneHCID 516892Sodium Bicarbonate

Product 1

HCID 187966231-(1-Methyl(4-piperidyl))-6-nitroindoline

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane. N-Methyl-4-piperidone (5 g) was added to the mixture, followed by NaHB(OAc)3 (12 g) and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. A saturated NaHCO3 (200 mL) solution was added to the reaction mixture and stirred for 1 h. The resulting mixture was separated by separation funnel. The organic layer was extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford orange oil. MS: 262 (M+1). Calc'd. for C14H19N3O2—261.3.

Workup

  1. stirringstirred for 1 h
  2. customThe resulting mixture was separated by separation funnel
  3. extractionThe organic layer was extracted once with saturated NaHCO3 solution and once with brine
  4. dry with materialThe resulting organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography on silica gel with 2:1 EtOAc
  8. customMeOH to afford orange oil

Sources & evidence

ORD record
ord-f2545be5cd0948448e5dd286c3f52b7b
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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