Furan → HCID 22993562, compound

HRID 1167722Notes

Reaction equation

HRID 1167722 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-6bee02392e5444d78c4d2cddb9411113
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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