4-Methyl-3-nitrobenzoic acid → HCID 16962626, compound

HRID 2424393Notes

Reaction equation

HRID 2424393 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C([O:18][C:19](N1CCNCC1)=[O:20])CCC.[CH2:27](N(CC)CC)C.CN(C(ON1N=NC2C=C[CH:47]=[CH:48][C:43]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:56]1[CH:61]=[N:60][C:59]2N(O)N=[N:64][C:58]=2C=1>CN(C=O)C.O>[C:48]([O:20][C:19]([N:60]1[CH2:61][CH2:56][N:64]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH2:58][CH2:59]1)=[O:18])([CH3:47])([CH3:43])[CH3:27]

Participants

8

Reactant 5

HCID 73194-Methyl-3-nitrobenzoic acidHCID 8471TriethylamineHCID 181649HOAtHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21963126Butyl piperazine-1-carboxylate

Product 1

HCID 16962626HCID 16962626, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-3-nitro-benzoic acid (300 mg, 2.76 mmol), N -butoxycarbonyl-piperazine (340 mg, 1.83 mmol) in DMF (3.0 mL), triethylamine (300 μL, 3.59 mmol), TBTU (800 mg, 2.49 mmol) and HOAt (270.5 mg, 1.99 mmol) are added and stirred at room temperature for 24 hours. The mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with water and then brine, dried over magnesium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n -hexane:ethyl acetate=5:1) to afford 4-(4-methyl-3-nitrobenzoyl)-piperazine-1-carboxylic acid tert-butyl ester as a colorless solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified with silica gel column chromatography (n -hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-661db8696dcf45e5826a0e01137d209a
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

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