Furan → HCID 22993562, compound

HRID 1275238Notes

Reaction equation

HRID 1275238 reaction equation
O[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Cl-].[Al+3].[Cl-].[Cl-].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:8]1([C:2]2([C:15]3[O:14][CH:18]=[CH:17][CH:16]=3)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 8029FuranHCID 963874-Phenylpiperidin-4-olHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22993562HCID 22993562, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-4-phenyl-piperidine(0.50 g, 2.8 mmol) in 10 ml of CH2Cl2 at 25° C. was added furan (0.40 ml, 5.6 mmol) and aluminum chloride (0.75 g, 5.6 mmol) in a portion and the resulting heterogeneous solution was stirred for 3 h. Reaction mixture was poured into cold aqueous NaHCO3 and extracted with EtOAc. Organic layer was dried over Na2SO4 and concentrated in vacuo to provide oily residue, which was purified by column chromatography (30% NH3 sat'd MeOH/EtOAc) to yield 0.48 g (76%) of the desired product as an oil.

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialOrganic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto provide oily residue, which
  6. customwas purified by column chromatography (30% NH3 sat'd MeOH/EtOAc)

Sources & evidence

ORD record
ord-8f98ce6c20f742fa8fcc59b90bfb4bce
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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