Potassium Carbonate → 6-{4-[2-(4-Nitrophenyl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466139Notes

Reaction equation

HRID 1466139 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1.I[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+]>CN(C=O)C>[N+:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][N:6]2[CH2:5][CH2:4][N:3]([CH:8]3[CH2:17][CH2:16][C:15]4[CH:14]=[C:13]([C:18]#[N:19])[CH:12]=[CH:11][C:10]=4[CH2:9]3)[C:2](=[O:1])[CH2:7]2)=[CH:24][CH:25]=1)([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113464461-(2-Iodoethyl)-4-nitrobenzeneHCID 895249666-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 715256866-{4-[2-(4-Nitrophenyl)ethyl]-2-oxopiperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (20 mg, 0.078 mmol) in DMF (1 mL) was added 1-(2-Iodoethyl)-4-nitrobenzene (26 mg, 0.094 mmol) and K2CO3 (43 mg, 0.31 mmol). The mixture was allowed to stir at RT for 16 hours. LC showed product formation. The desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA). LC-MS (IE, m/z): 405 [M+1]+.

Workup

  1. customThe desired product was purified by mass-directed reverse phase HPLC (AcCN-Water with 0.1% TFA)

Sources & evidence

ORD record
ord-ad1bfe5f6ef240e1b7d496ddd11a5541
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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