6-Nitroindoline → 1-(1-Methyl(4-piperidyl))-6-nitroindoline

HRID 238503

Reaction equation

HRID 238503 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.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClC(Cl)C.CC(O)=O>[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

7

Reactant 4

HCID 297576-NitroindolineHCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 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 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) 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 an orange oil. MS: 262 (M+1). Calc'd. for C14H19N3O2—261.32.

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 an orange oil

Sources & evidence

ORD record
ord-7d1fd85e774f4ec59f2291df1b4171fd
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Linked notes

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