Potassium Carbonate → HCID 12052631, compound

HRID 1264083Notes

Reaction equation

HRID 1264083 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:16][NH2:17].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:16][NH:17][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 12052630HCID 12052630, compound

Product 1

HCID 12052631HCID 12052631, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoronitrobenzene (0.358 mL, 3.4 mmol, 1.0 eq.), 3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl amine (750 mg, 3.4 mmol) and anhydrous potassium carbonate (471 mg, 3.4 mmol, 1.0 eq.) were combined in dry THF (35 mL) then allowed to stir 48 h at ambient temperature. The reaction mixture was filtered through a bed of diatomaceous earth then the solvent was removed under reduced pressure. The crude oil was purified by flash chromatography (eluting with 20:1 CHCl3:MeOH, 0.5% TEA) to give the desired product as a right orange oil (676 mg, 58%).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of diatomaceous earth
  2. customthe solvent was removed under reduced pressure
  3. customThe crude oil was purified by flash chromatography (eluting with 20:1 CHCl3:MeOH, 0.5% TEA)

Sources & evidence

ORD record
ord-bcb4c54208c74c9fa752652beeb9c5b7
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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