Ammonium formate → 4-(4-Benzofuranyl)-piperidine

HRID 331398Notes

Reaction equation

HRID 331398 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[CH:4]=[CH:3]1.BrC1C2C=COC=2C=CC=1.CC1(C)C(C)(C)OB(C2CCN(C(OC(C)(C)C)=O)CC=2)O1.C([O-])=O.[NH4+]>[Pd].CO>[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[CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 2723923Ammonium formateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 151587214-Bromo-1-benzofuranHCID 679723964-(4-Benzofuranyl)-1,2,3,6-tetrahydro-pyridine hydrochloride

Product 1

HCID 679724334-(4-Benzofuranyl)-piperidineYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of 4-(4-benzofuranyl)-1,2,3,6-tetrahydro-pyridine hydrochloride [CAS-No. 158984-66-8] (2.05 g, 8.7 mmol), prepared from commercially available 4-bromo-benzofurane [CAS-No. 128868-60-0] and commercially available tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate, palladium on carbon (10%, 0.46 g, 0.44 mmol), ammonium formate (2.74 g, 43.5 mmol) and MeOH (79 ml) was heated at reflux conditions for 1 h, cooled to RT, filtrated and evaporated. Saturated sodium bicarbonate solution (50 ml) was added to the residue, and the inorganic layer was extracted with dichloromethane (2×40 ml). The combined organic layers were washed with brine (40 ml), dried (MgSO4) and evaporated to yield 4-(4-benzofuranyl)-piperidine as a colorless oil (1.65 g, 94%), MS (ISP) m/z=202.3 [(M+H)+].

Workup

  1. temperaturewas heated
  2. temperatureat reflux conditions for 1 h
  3. filtrationfiltrated
  4. customevaporated
  5. additionSaturated sodium bicarbonate solution (50 ml) was added to the residue
  6. extractionthe inorganic layer was extracted with dichloromethane (2×40 ml)
  7. washThe combined organic layers were washed with brine (40 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-e092dacc93f7473a9e3f287339c0bdcf
Source dataset
uspto-grants-2014_11
Patent number
US08877778B2

Reaction notes

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