1-Methylpiperazine → HCID 59313927, compound

HRID 889438Notes

Reaction equation

HRID 889438 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12]>C(Cl)Cl>[NH2:8][C:9]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:10]=1[C:11]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:12]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 214891672-Amino-4-nitrobenzoyl chloride

Product 1

HCID 59313927HCID 59313927, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methylpiperazine (2.5 g, 24.96 mmol) in DCM (30 mL) at 0° C. was added a solution of Intermediate 69A (1.13 g, 5.63 mmol) in DCM (10 mL) slowly. The reaction was stirred at room temperature for 1 hour. The reaction mixture was washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM) to give Intermediate 69B (0.77 g, 52%) as a yellow oil. HPLC: Rt=0.360 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). MS (ES): m/z=265 [M+H]+.

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-19e3054b587d42aeb2c5d80f10384392
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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