1-Piperazinecarboxylic acid, ethyl ester → HCID 86679353, compound

HRID 1498960Notes

Reaction equation

HRID 1498960 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].[CH2:16](N(CC)CC)C.[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32]N[CH2:30][CH2:29]1)=[O:27])[CH3:24]>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[CH:12][C:2]([CH:16]2[CH2:32][CH2:33][N:28]([C:26]([O:25][CH2:23][CH3:24])=[O:27])[CH2:29][CH2:30]2)=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8471TriethylamineHCID 21277355Ethyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 86679353HCID 86679353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-fluoro-3-nitrobenzoate (10.0 g, 46.91 mmol) prepared in the Step 1-1-1 was dissolved in ethanol (100 ml). To the solution, triethylamine was added and then ethoxycarbonylpiperazine (49.26 mmol) was added, and the mixture was stirred at a room temperature for 18 hours. After the mixture was concentrated, ethyl acetate was added thereto. The resulting mixture was washed with a saturated sodium bicarbonate solution and a saturated saline solution in order. The washed product was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1-1:1) to give the title compound (17.4 g, quantitative) as a yellowish-brown oily substance.

Workup

  1. concentrationAfter the mixture was concentrated
  2. additionethyl acetate was added
  3. washThe resulting mixture was washed with a saturated sodium bicarbonate solution
  4. dry with materialThe washed product was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1-1:1)

Sources & evidence

ORD record
ord-575b7138db9843328adb640e355982f2
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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