Piperidine → HCID 57470218, compound

HRID 2370251Notes

Reaction equation

HRID 2370251 reaction equation
C(=O)(OC)[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([F:12])=[CH:5][C:4]=1[C:13]([CH3:16])([CH3:15])[CH3:14].N1CCCCC1>C(Cl)Cl>[C:13]([C:4]1[CH:5]=[C:6]([F:12])[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[OH:2])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 574702162-Tert-butyl-4-fluoro-5-nitrophenyl methyl carbonate

Product 1

HCID 57470218HCID 57470218, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-tert-butyl-4-fluoro-5-nitrophenyl methyl carbonate (C-7-a) (1.08 g, 4 mmol) in CH2Cl2 (40 mL) was added piperidine (3.94 mL, 10 mmol). The mixture was stirred at room temperature for 1 h and extracted with 1N NaOH (3×). The aqueous layer was acidified with 1N HCl and extracted with diethyl ether. The ether extract was washed with brine, dried (MgSO4) and concentrated to give 2-tert-butyl-4-fluoro-5-nitrophenol (530 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δ 10.40 (s, 1H), 7.49 (d, J=6.8 Hz, 1H), 7.25 (d, J=13.7 Hz, 1H), 1.36 (s, 9H).

Workup

  1. extractionextracted with 1N NaOH (3×)
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5b78e3cd9924aca9feaec1ea9b1f8c8
Source dataset
uspto-grants-2014_04
Patent number
US08710075B2

Reaction notes

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