4-Iodobenzoic acid → 1-(4-Iodobenzoyl)-4-methylpiperazine

HRID 1486823Notes

Reaction equation

HRID 1486823 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>C(Cl)Cl.CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:30]2[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]2)=[O:8])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 120854-Iodobenzoic acidHCID 531671-MethylpiperazineHCID 65578Oxalyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 8799091-(4-Iodobenzoyl)-4-methylpiperazineYield 99.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

4-Iodobenzoic acid (500 mg, 2.02 mmol) and DMF (50 uL) were dissolved in DCM (24 mL), oxalyl chloride (0.18 mL, 2.12 mmol) was added drop-wise and the reaction mixture was stirred for 30 min. DIPEA (0.42 mL, 2.42 mmol) and a solution of N-methylpiperazine (222 mg, 2.22 mmol) in DCM (1 mL) were added and the reaction mixture was stirred for 30 min, washed with sat aq NaHCO3 (2×75 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (660 mg, 99.2%) as a yellow solid. LCMS (ES+): 331.0 [MH]+. HPLC: Rt 4.05 min, 99.6% purity.

Workup

  1. stirringthe reaction mixture was stirred for 30 min
  2. washwashed with sat aq NaHCO3 (2×75 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a4c68d145b84430d9ce61d4782df7905
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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