1-Methylpiperazine → 3-Methoxy-4-(4-methyl-piperazin-1-ylmethyl)-nitrobenzene

HRID 601512Notes

Reaction equation

HRID 601512 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:4]=1[CH2:5][N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 27595992-Methoxy-4-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 574214773-Methoxy-4-(4-methyl-piperazin-1-ylmethyl)-nitrobenzene

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a round bottom flask or vial containing 2-methoxy-4-nitro-benzaldehyde (1.0 g, 5.5 mmol), add dichloroethane (40 mL), 1-methylpiperazine (1.0 ml, 8.3 mmol), and sodium triacetoxyborohydride (3.5 g, 16.5 mmol). Stir at room temperature overnight. Quench with saturated aqueous NaHCO3 and extract with CH2Cl2 (1×) and EtOAc (2×). Combine the organic portions, dry over MgSO4, filter, and concentrate under vacuum. Purify the residue by flash chromatography on silica gel using a gradient of MeOH (0.005% NH4OH)/CH2Cl2 (5% to 10%) to give the title compound. MS (ES+) 266.0 (M+1)+. 1H NMR (CDCl3): δ 7.80 (dd, J=8 Hz, 2 Hz, 1H), 7.66 (d, J=2 Hz, 1H), 7.56 (J=8 Hz, 1H), 3.89 (s, 3H), 3.58 (s, 2H), 2.52 (br. 4H), 2.45 (br, 2H), 2.28 (s, 3H).

Workup

  1. customQuench with saturated aqueous NaHCO3
  2. extractionextract with CH2Cl2 (1×) and EtOAc (2×)
  3. dry with materialCombine the organic portions, dry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify the residue by flash chromatography on silica gel using a gradient of MeOH (0.005% NH4OH)/CH2Cl2 (5% to 10%)

Sources & evidence

ORD record
ord-67a5e924f34b42a3bc69d9a32f7794f4
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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