1-Methylpiperazine → [2-(4-Methylpiperazino)-5-nitrophenyl]methanol

HRID 1190863Notes

Reaction equation

HRID 1190863 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH2:4][OH:5].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C1COCC1>[CH3:13][N:14]1[CH2:19][CH2:18][N:17]([C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[CH2:4][OH:5])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 4437169(2-Fluoro-5-nitrophenyl)methanol

Product 1

HCID 25918812[2-(4-Methylpiperazino)-5-nitrophenyl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-5-nitrobenzyl alcohol (1 g, 5.84 mmol) and N-methylpiperazine (1.29 mL, 2 eq) were heated at 130° C. for 1 h. The reaction mixture was then diluted with 25 mL of THF and washed with a saturated aqueous solution of Na2CO3 and then with brine. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was thoroughly washed with pentane and filtered off to yield expected compound as an orange powder (1.38 g, 94% yield). m/z (ESI) 252.1 [M+H]+.

Workup

  1. washwashed with a saturated aqueous solution of Na2CO3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. washThe residue was thoroughly washed with pentane
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-a7a4d715d5a94319bcd29bd81c8f21d4
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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