2-Piperidone → HCID 22021620, compound

HRID 717784Notes

Reaction equation

HRID 717784 reaction equation
N([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O>C(O)(=O)C.[Zn]>[CH:10]1[C:11]2[C:15]3[CH2:14][NH:13][CH2:18][CH2:17][C:16]=3[N:3]3[C:12]=2[C:7]([CH2:6][CH2:5][CH2:4]3)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 126652-PiperidoneHCID 8175751,2,3,4-Tetrahydro-1-nitrosoquinoline

Product 1

HCID 22021620HCID 22021620, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

1-Nitroso-1,2,3,4-tetrahydroquinoline (5.8 g, 0.0357 mol) was dissolved in acetic acid (50 mL). NH-piperidone (7.97 g, 0.0464 mol) was added and cooled to 0° C. Zinc dust was added (11.67 g, 0.1785 mol) in small portions. After addition, the reaction mixture was heated at 85° C. for 1 h. The reaction was monitored by TLC & LCMS. After completion of reaction, the mixture was filtered and the filtrate neutralized by aq. NaHCO3. The mixture was extracted with EtOAc (3×200 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 6.2 g product that was purified by column chromatography using 100-200 mesh silica and 5-7% MeOH in DCM+2 drops NH4OH to give pure product.

Workup

  1. additionAfter addition
  2. temperaturethe reaction mixture was heated at 85° C. for 1 h
  3. customAfter completion of reaction
  4. filtrationthe mixture was filtered
  5. extractionThe mixture was extracted with EtOAc (3×200 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c7351192a2a54ee5b8704c3edcefc033
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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