Acetic Acid → 1-(4-Fluorobenzyl)piperidine

HRID 2361637Notes

Reaction equation

HRID 2361637 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.CC(O)=O>ClCCCl>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 43637561-(4-Fluorobenzyl)piperidineYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of 4-fluorobenzaldehyde (500 mg, 4.0 mmol) in DCE (3 ml) at RT was added piperidine (309 mg, 3.6 mmol) followed by AcOH (242 mg, 4.0 mmol). The solution was stirred at RT for 2 h, and then STAB (1.3 g, 6.05 mmol) was added in one portion. The resulting mixture was stirred at RT overnight and then quenched with saturated NaHCO3 (10 ml). The organic layer was separated, dried (Na2SO4), filtered and concentrated at reduced pressure. Purification by silica flash column chromatography (eluting with DCM/MeOH/NH3 90:10:1) provided the title compound as colourless oil (650 mg, 95%).

Workup

  1. additionSTAB (1.3 g, 6.05 mmol) was added in one portion
  2. stirringThe resulting mixture was stirred at RT overnight
  3. customquenched with saturated NaHCO3 (10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customPurification
  9. washby silica flash column chromatography (eluting with DCM/MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-51249adee3834c9494320d89e3548acf
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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