Piperidine → HCID 66728514, compound

HRID 518765Notes

Reaction equation

HRID 518765 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CC(O)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66728514HCID 66728514, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-fluoro-4-nitrobenzaldehyde (4.85 g, 28.7 mmol), piperidine (3.12 mL, 31.5 mmol) and 20 drops of AcOH in DCM was added sodium triacetoxyborohydride (6.69 g, 31.5 mmol), and the resulting suspension was stirred at RT for 30 minutes. The reaction was made basic with 2N aqueous NaOH, and extracted with DCM. The organic layer was washed with brine and was dried over sodium sulfate, filtered and concentrated in vacuo to yield a red oil. The residual oil was purified via MPLC, eluting with a gradient of 0-100% EtOAc in hexane to yield 1-(3-fluoro-4-nitrobenzyl)piperidine (3.98 g, 16.70 mmol, 58.2% yield) as an orange oil.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a red oil
  7. customThe residual oil was purified via MPLC
  8. washeluting with a gradient of 0-100% EtOAc in hexane

Sources & evidence

ORD record
ord-309246382b44426bbb1cf008a67d8c61
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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