Ammonium formate → 4-Benzo[1,3]dioxol-4-yl-piperidine

HRID 1909357Notes

Reaction equation

HRID 1909357 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)[C:5]=2[O:4][CH2:3]1.C([O-])=O.[NH4+]>CO.[Pd]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 706564464-(Benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 706572904-Benzo[1,3]dioxol-4-yl-piperidineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C 10% (169 mg, 159 μmol,) was added to a solution of 4-(benzo[1,3]dioxol-4-yl)-1,2,3,6-tetrahydropyridine hydrochloride (760 mg, 3.17 mmol) and ammonium formate (1.00 g, 15.9 mmol) in methanol (28.8 ml) under argon. After refluxing for 60 min the reaction mixture was cooled to room temperature, filtrated and concentrated under reduced pressure. Saturated sodium bicarbonate solution was added to the residue and the mixture was extracted with dichloromethane (3×25 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to yield the title compound as a white solid (0.654 grs, 100%). MS (ISP) m/z=206.0[(M+H)+].

Workup

  1. temperatureAfter refluxing for 60 min the reaction mixture
  2. filtrationfiltrated
  3. concentrationconcentrated under reduced pressure
  4. additionSaturated sodium bicarbonate solution was added to the residue
  5. extractionthe mixture was extracted with dichloromethane (3×25 mL)
  6. dry with materialThe organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae532a8722ee49fe9ab6be0c258bebc9
Source dataset
uspto-grants-2013_12
Patent number
US08598357B2

Reaction notes

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