Triethylamine → 1-[2-(4-Bromophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine

HRID 1519557Notes

Reaction equation

HRID 1519557 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]Br)=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C=O)C>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][N:15]2[CH2:14][CH2:13][N:12]([CH2:11][CH2:10][C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:17][CH2:16]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110108254-Bromophenethyl bromideHCID 149859651-[2-(4-Nitrophenyl)ethyl]piperazine

Product 1

HCID 675134121-[2-(4-Bromophenyl)ethyl]-4-[2-(4-nitrophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[2-(4-nitrophenyl)ethyl]piperazine (300 mg, 1.3 mmol), 1-bromo-4-(2-bromoethyl)benzene (400 mg, 1.5 mmol), and triethylamine (0.89 mL, 6.4 mmol) in DMF (5 mL) was heated to 60° C. for 16 hours. LC showed formation of the desired product. The desired product was purified by silica gel chromatography (10% MeOH in EtOAc). LC-MS (IE, m/z): 420 (M+1)+.

Sources & evidence

ORD record
ord-15297085885344ea87f2b6c3ea2b18b4
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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