Piperidine → Ethyl 3-nitro-4-(piperidin-1-yl)benzoate

HRID 1498893Notes

Reaction equation

HRID 1498893 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].C(N(CC)CC)C.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)(O)[O-].[Na+]>C(O)C>[N+:13]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 12493642Ethyl 3-nitro-4-(piperidin-1-yl)benzoateYield 106.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-fluoro-3-nitrobenzoate (160 g, 0.752 mol) prepared in the Step 1-1-1 was suspended in ethanol (500 ml). Triethylamine (91.4 g, 0.903 mol) was added to the suspension, and under an ice cooling, piperidine (76.9 g, 0.903 mol) was slowly added thereto. After the mixture was stirred at a room temperature for 2 hours, a saturated sodium bicarbonate solution was added to the mixture, and the resulting mixture was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and a saturated saline solution in order, and then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 to 3:1) to give the title compound (222 g, quantitative) as a poppy-red oily substance.

Workup

  1. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution
  3. dry with materiala saturated saline solution in order, and then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 to 3:1)

Sources & evidence

ORD record
ord-08aa21fb66624415afd2f8d3f01ffd81
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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