1-Methyl-4-piperidone → HCID 21959544, compound

HRID 238509Notes

Reaction equation

HRID 238509 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[CH3:15][N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[CH2:3]1

Participants

7

Reactant 4

HCID 740491-Methyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 21959544HCID 21959544, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethyl-6-nitroindoline (0.8 g) was dissolved in CH2Cl2 (50 mL), N-methyl-4-piperidone (1 g) was added to the mixture, followed by 2.5 g NaBH(OAc)3 and glacial AcOH (1 mL). The mixture was stirred at RT overnight. Saturated NaHCO3 solution (50 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 9:1 EtOAc:MeOH to afford the title compound as an orange oil. MS: 290 (M+1). Calc'd. for C16H23N3O2—289.37.

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 9:1 EtOAc

Sources & evidence

ORD record
ord-c89a4b6eb81c44bc9ef749901fbe5e62
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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