Ethanol → HCID 58032090, compound

HRID 1429225Notes

Reaction equation

HRID 1429225 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.[Cl-].[NH4+].CCO.C1COCC1>[Fe].O>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:13][CH2:14][CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH2:17]1)[NH2:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 49760180HCID 49760180, compound

Product 1

HCID 58032090HCID 58032090, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

In a 500 mL round-bottom flask was added 1-(2,6-difluoro-4-nitrophenyl)-4-phenylpiperidine (4.53 g, 14.23 mmol), iron (3.97 g, 71.2 mmol), and ammonium chloride (1.142 g, 21.35 mmol) in a solvent mixture of EtOH (60 mL)/THF (60 mL)/water (20 mL). The mixture was refluxed for 3 hours with vigorous stirring, cooled, filtered through diatomaceous earth and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and evaporated to give the title compound as yellow solid (3.93 g, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.63-1.81 (m, 4 H) 2.54-2.64 (m, 1 H) 2.95-3.03 (m, 2 H) 3.09 (t, J=10.57 Hz, 2 H) 5.42 (s, 2 H) 6.10-6.21 (m, 2 H) 7.15-7.22 (m, 1 H) 7.25-7.34 (m, 4 H); MS (ESI+) m/z 289 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 3 hours with vigorous stirring
  2. temperaturecooled
  3. filtrationfiltered through diatomaceous earth
  4. concentrationthe filtrate was concentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-40f071b37751497890e1b97b4b15998a
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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