4-Nitrophenethyl bromide → 1,4-Bis[2-(4-nitrophenyl)ethyl]piperazine

HRID 1519554Notes

Reaction equation

HRID 1519554 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1>CN(C=O)C>[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][N:16]([CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=3)[CH2:17][CH2:18]2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 792664-Nitrophenethyl bromideHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 523378371,4-Bis[2-(4-nitrophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (30 mg, 0.11 mmol) in DMF (2 mL) was added 1-(2-bromoethyl)-4-nitrobenzene (31 mg, 1.3 mmol) and TEA (46 uL, 0.33 mmol). The mixture was heated to 80° C. for 16 hours. LC showed some desired product at that point. The desired 1,4-bis[2-(4-nitrophenyl)ethyl]piperazine was purified by mass-directed HPLC. LC-MS (IE, m/z): 385 [M+1]+. (0.052 μM)

Sources & evidence

ORD record
ord-8a79e3ec105c4f4388ce75a52946219b
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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