Benzaldehyde → N-benzyl-2-(4-benzoylpiperazin-1-yl)-5-nitrobenzenamine

HRID 1966454Notes

Reaction equation

HRID 1966454 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1.[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:25]([NH:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17](=[O:18])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:15][CH2:16]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58425640(4-(2-Amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone

Product 1

HCID 58425594N-benzyl-2-(4-benzoylpiperazin-1-yl)-5-nitrobenzenamineYield 20%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of (4-(2-amino-4-nitrophenyl)piperazin-1-yl)(phenyl)methanone (0.4 g, 1.2 mmol) and benzaldehyde (0.18 ml, 1.8 mmol) in 15 ml dichloroethane was stirred for 10 min, followed by the addition of sodium triacetoxyborohydride (0.78 g, 3.68 mmol). The mixture was stirred overnight under argon atmosphere. The reaction was quenched with water and extracted with ethyl acetate (3×20 ml), followed by drying over anhydrous sodium sulfate. N-benzyl-2-(4-benzoylpiperazin-1-yl)-5-nitrobenzenamine (0.1 g, 19%) was obtained by flash column chromatograph (50% ethyl acetate in hexanes). 1H NMR (500 MHz, CDCl3) δ (ppm) 3.00-3.60 (d, br, 8H), 4.44 (d, J=5.5 Hz, 2H), 5.04 (t, J=5.5 Hz, 1H), 7.06 (d, J=8.6 Hz, 1H), 7.34-7.65 (m, 11H), 7.67 (dd, J=8.6, 2.5 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ (ppm) 48.6, 51.3, 105.5, 113.6, 119.3, 127.6, 127.7, 128.2, 129.1, 129.4, 130.5, 135.9, 138.7, 143.4, 144.3, 146.0, 171.1.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialby drying over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-0b8ba7a6b08c4263a7b2718b67cb04ac
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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