Sodium Hydroxide → 1-[2-(4-Nitrophenyl)ethyl]-4-[1-(4-nitrophenyl)propan-2-yl]piperazine

HRID 1519570Notes

Reaction equation

HRID 1519570 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=O)[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1)([O-:17])=[O:16].C([BH3-])#N.[Na+].[OH-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][N:29]([CH:11]([CH3:12])[CH2:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:30][CH2:31]2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2193671-(4-Nitrophenyl)propan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 714582151-[2-(4-Nitrophenyl)ethyl]-4-[1-(4-nitrophenyl)propan-2-yl]piperazine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

4-Nitrophenylacetone (33 mg, 0.18 mmol) and 1-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (50 mg, 0.18 mmol) were added to Titanium(IV) Isopropoxide (110 μl, 0.37 mmol) and stirred for 1 hour. Ethanol was added followed by sodium cyanoborohydride (23 mg, 0.37 mmol) and stirred at room temperature overnight. Poured into 1N NaOH and extracted with ethyl acetate then washed with brine, dried and evaporated to dryness. The residue was purified by mass directed HPLC to yield 1-[2-(4-nitrophenyl)ethyl]-4-[1-(4-nitrophenyl)propan-2-yl]piperazine. LC-MS (IE, m/z): 399 [M+1]+. 1H-NMR (500 MHz, DMSO) δ ppm 8.19 (t, J=8.5 Hz, 4H), 7.56 (d, J=9.7 Hz, 2H), 7.54 (d, J=9.7 Hz, 2H), 2.76-4.4 (m, 15H), 1.02 (d, J=6.1 Hz, 3H). (0.24 μM)

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washthen washed with brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by mass

Sources & evidence

ORD record
ord-9632a0b3f4dd44f3bed702fe754e73c9
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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