Potassium Carbonate → HCID 60509567, compound

HRID 1519559Notes

Reaction equation

HRID 1519559 reaction equation
Cl.[CH3:2][CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH3:2][CH:3]1[CH2:8][N:7]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)[CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 67513564HCID 67513564, compound

Product 1

HCID 60509567HCID 60509567, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a flask charged with 2-methyl-[2-(4-nitrophenyl)ethyl]piperazine hydrochloride (40 mg, 0.14 mmol) and a stir bar was added 1-(2-bromoethyl)-4-nitrobenzene (65 mg, 0.28 mmol), tetrabutylammonium iodide (5.2 mg, 0.014 mmol), K2CO3 (48 mg, 0.35 mmol), and DMF (2 mL). The mixture was heated to 80° C. for 16 hours. LC showed formation of the desired product, which was separated by mass-directed HPLC. LC-MS (IE, m/z): 399 [M+1]+. (0.14 μM)

Sources & evidence

ORD record
ord-088af88bda924817b095f39d40b7f6de
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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