1-Methylpiperazine → HCID 67183501, compound

HRID 1966437Notes

Reaction equation

HRID 1966437 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN1C(=O)CCC1>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:7]=2)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 2386965-bromo-2-nitro-n-phenylaniline

Product 1

HCID 67183501HCID 67183501, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-nitro-N-phenylbenzenamine (1.0 g, 3.4 mmol) and 1-methylpiperazine (1.50 ml, 13.6 mmol) in 15 ml NMP was heated at 100° C. for 16 hours. The reaction was quenched with 100 ml water. The mixture was extracted with ethyl acetate (3×30 ml) and dried over anhydrous sodium sulfate. 5-(4-methylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (0.50 g, 49%) was obtained by flash column chromatograph (10% ethanol in dichloromethane). 5-(4-methylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine hydrochloride was made by bubbling HCl gas in its ethyl ether solution and crystallized. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 2.75 (s, 3H), 3.03 (dd, J=12.9, 12.0 Hz, 2H), 3.29 (dd, J=11.9, 12.9 Hz, 2H), 3.42 (d, J=12.0 Hz, 2H), 3.90 (d, J=12.9, Hz, 2H), 6.48 (d, J=1.5 Hz, 1H), 6.65 (dd, J=2.6, 9.7 Hz, 1H), 7.2 (m, 1H), 7.23-7.45 (m, 4H), 8.06 (d, J=9.7 Hz, 1H), 9.72 (s, 1H), 11.27 (s, 1H). 13C NMR (125 MHz, DMSO-d6): δ (ppm) 40.0, 43.4, 51.5, 96.7, 106.8, 123.5, 124.9, 128.3, 129.6, 138.9, 144.2, 154.5.

Workup

  1. customThe reaction was quenched with 100 ml water
  2. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-dedb415312a2406bbef4466dfcfa3c03
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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