Potassium Carbonate → HCID 86694469, compound

HRID 1519569Notes

Reaction equation

HRID 1519569 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.Br[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][N:3]2[CH2:2][CH:1]3[N:8]([CH2:10][CH2:11][C:12]4[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=4)[CH:5]([CH2:6][CH2:7]3)[CH2:4]2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 124305873,8-Diazabicyclo[3.2.1]octane

Product 1

HCID 86694469HCID 86694469, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,8-diazabicyclo[3.2.1]octane (55 mg, 0.49 mmol), 1-(2-bromoethyl)-4-nitrobenzene (340 mg, 1.5 mmol), tetrabutylammonium iodide (18 mg, 0.049 mmol), and K2CO3 (270 mg, 2.0 mmol) in DMF (2 mL) 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): 411 [M+1]+. (0.19 μM)

Sources & evidence

ORD record
ord-985744a5659f43f5a38f4e12abe77ed6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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