Potassium Carbonate → HCID 21906430, compound

HRID 1882977Notes

Reaction equation

HRID 1882977 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].F[C:22]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25]>CS(C)=O.CCOC(C)=O>[N+:32]([C:29]1[CH:30]=[CH:31][C:22]([NH:14][CH2:13][CH:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH2:12][CH2:11]2)=[C:23]([CH:28]=1)[C:24]([O:26][CH3:27])=[O:25])([O-:34])=[O:33]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamineHCID 11217860Methyl 2-Fluoro-5-nitrobenzoate

Product 1

HCID 21906430HCID 21906430, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-pyridyl)piperidine-4-methylamine (1.13 g, 5.92 mmol) and potassium carbonate (816 mg, 5.92 mmol) in dimethyl sulfoxide (12 mL) was treated with methyl 2-fluoro-5-nitrobenzoate (1.18 g, 5.92 mmol). After 17 h, the mixture was cooled, diluted with EtOAc, and filtered. The filtrate was concentrated and partitioned between EtOAc and 10% HCl. The aqueous layer was washed with EtOAc (1×), pH adjusted (>10) by addition of NaOH, and washed with EtOAC (3×). The combined extracts were washed with H2O (5×), brine, dried (sodium sulfate), and concentrated. The residue was purified by column chromatography (SiO2, 1 to 3% [2 N NH3 in MeOH]:chloroform) yielding 920 mg (42%) of the title compound.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between EtOAc and 10% HCl
  5. washThe aqueous layer was washed with EtOAc (1×)
  6. additionby addition of NaOH
  7. washwashed with EtOAC (3×)
  8. washThe combined extracts were washed with H2O (5×), brine
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography (SiO2, 1 to 3% [2 N NH3 in MeOH]:chloroform)

Sources & evidence

ORD record
ord-097c6be5a78f4dd8bb0c2f4ad18f65be
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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