Potassium Carbonate → HCID 56971324, compound

HRID 1519563Notes

Reaction equation

HRID 1519563 reaction equation
Br.Br.[C@H:3]12[CH2:9][C@H:6]([NH:7][CH2:8]1)[CH2:5][NH:4]2.Br[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][N:4]2[CH2:5][C@@H:6]3[CH2:9][C@H:3]2[CH2:8][N:7]3[CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 14612497(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide

Product 1

HCID 56971324HCID 56971324, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (1S,4S)-2,5-diazabicyclo[2.2.1]heptane dihydrobromide (60 mg, 0.23 mmol), 1-(2-bromoethyl)-4-nitrobenzene (210 mg, 0.92 mmol), tetrabutylammonium iodide (8.5 mg, 0.023 mmol), and K2CO3 (128 mg, 0.92 mmol) in DMF (2 mL) was heated to 60° C. for 16 hours. LC showed formation of the desired product, which was separated by mass-directed HPLC. LC-MS (IE, m/z): 397 [M+1]+. (0.11 μM)

Sources & evidence

ORD record
ord-d75e27392a0c4c4280e87847c61c443e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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