Ethylenediamine → 2-(3-(4-Nitrophenyl)propyl)-4,5-dihydro-1H-imidazole

HRID 1192882Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH:13]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]([NH2:18])[CH2:16][NH2:17].C1C(=O)N(Br)C(=O)C1>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[NH:17][CH2:16][CH2:15][N:18]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

The mixture of 4-(4-Nitrophenyl)butanal (64) (0.28 g, 1.45 mmol) and ethylene diamine (0.1 mL, 1.59 mmol) in dry dichloromethane (10 mL) was stirred at 0° C. for 30 min under argon. NBS (0.26 g, 1.59 mmol) was added to the mixture and the resulting solution was stirred overnight at 21° C. Reaction was quenched by the addition of saturated NaHCO3 solution. The mixture was extracted with dichloromethane. The organic layer was dried over MgSO4, and evaporated in vacuo. The residue was purified by flash column chromatography (ethanol:ethyl acetate:triethylamine, 1:1:0.2) to give 2-(3-(4-Nitrophenyl)propyl)-4,5-dihydro-1H-imidazole (62) (0.26 g, 76%): 1H NMR δ 8.14 (d, 2H, J=8.7 Hz) 7.35 (d, 2H, J=8.7 Hz) 3.59 (s, 4H), 2.79 (t, 2H, J=7.7 Hz) 2.26 (t, 2H, J=7.4 Hz) 1.96-2.05 (m, 2H).

Workup

stirringthe resulting solution was stirred overnight at 21° C
customReaction
customwas quenched by the addition of saturated NaHCO3 solution
extractionThe mixture was extracted with dichloromethane
dry with materialThe organic layer was dried over MgSO4
customevaporated in vacuo
customThe residue was purified by flash column chromatography (ethanol:ethyl acetate:triethylamine, 1:1:0.2)

Sources & evidence

ORD record: ord-7ff50ba2a7694d5b9ce7e550c9d08300
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680291B2

Reaction notes

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