Ammonium formate → 4-(Benzofuran-3-yl)-piperidine

HRID 1409860Notes

Reaction equation

HRID 1409860 reaction equation
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=2)=[CH:3]1.C([O-])=O.[NH4+]>[Pd].CO>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:3]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 709452624-(Benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride

Product 1

HCID 214720424-(Benzofuran-3-yl)-piperidineYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 4-(benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride (1.57 g, 6.66 mmol), palladium on carbon (10%, 0.35 g, 0.33 mmol), ammonium formate (2.1 g, 33 3 mmol) and MeOH (61 ml) was heated at reflux conditions for 1 h, cooled to RT, filtrated and evaporated. The residue was diluted with ice-water (20 ml) and 3M NaOH (10 ml) and extracted with dichloromethane/methanol 9:1 (4×50 ml). The combined organic layers were washed with brine (1×25 ml), dried (MgSO4) and evaporated. The crude product (1.37 g) was purified by flash chromatography on silica gel (dichloromethane/methanol/NH4OH 65:10:1) to yield 4-(benzofuran-3-yl)-piperidine as a light yellow oil (1.1 g, 82%), MS (ISP) m/z=202.3 [(M+H)+].

Workup

  1. temperaturewas heated
  2. temperatureat reflux conditions for 1 h
  3. filtrationfiltrated
  4. customevaporated
  5. additionThe residue was diluted with ice-water (20 ml) and 3M NaOH (10 ml)
  6. extractionextracted with dichloromethane/methanol 9:1 (4×50 ml)
  7. washThe combined organic layers were washed with brine (1×25 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe crude product (1.37 g) was purified by flash chromatography on silica gel (dichloromethane/methanol/NH4OH 65:10:1)

Sources & evidence

ORD record
ord-8c02f083bb3541c2b0f17162337e4d38
Source dataset
uspto-grants-2014_12
Patent number
US08921397B2

Reaction notes

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