Piperidine → (2-Methoxy-4-nitro-phenyl)-piperidin-1-yl-methanone

HRID 1993522Notes

Reaction equation

HRID 1993522 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[B-](F)(F)(F)F.CN(C(O[N:28]1[C:33](=O)[CH:32]=[CH:31][CH:30]=[CH:29]1)=[N+](C)C)C.CCN(CC)CC.N1CCCCC1.C([O-])(O)=O.[Na+]>C(#N)C.C(Cl)Cl.O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:7]

Participants

10

Reactant 5

HCID 8082PiperidineHCID 8471TriethylamineHCID 757764-Nitro-o-anisic acidHCID 516892Sodium BicarbonateHCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate

Product 1

HCID 68540547(2-Methoxy-4-nitro-phenyl)-piperidin-1-yl-methanone

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled suspension of 2-methoxy-4-nitro-benzoic acid (5.915 g, 30 mmol) in acetonitrile (50 ml) and CH2Cl2 (40 ml) under N2-atmosphere, TPTU (8.912 g, 30 mmol) and NEt3 (8.36 ml, 60 mmol) is added. After stirring for 40 min, piperidine (3.26 ml, 33 mmol) is added and the reaction mixture is slowly warmed up to rt. After 16 h, AcOEt (0.5 L), water (0.4 L) and saturated NaHCO3 solution (0.2 L) is added, the aqueous phase separated off and extracted 3× with AcOEt. The organic layers are washed with 10% citric acid solution, water and brine, dried (Na2SO4) and concentrated. Crystallization from AcOEt/hexane yields the title compound: m.p.: 104° C.; 1H-NMR (DMSO-d6): 7.88 (dd, 1H), 7.84 (d, 1H), 7.47 (d, 1H), 3.93 (s, H3C), 3.7-3.5 (m, 2H), 3.07 (m, 2H), 1.64-1.5 (m, 4H), 1.42 (m, 2H).

Workup

  1. waitAfter 16 h
  2. customthe aqueous phase separated off
  3. extractionextracted 3× with AcOEt
  4. washThe organic layers are washed with 10% citric acid solution, water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customCrystallization from AcOEt/hexane

Sources & evidence

ORD record
ord-57d86001d6504b60a83d2a9435be8757
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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