Dimethylformamide → 5,6,7,8-Tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthalene

HRID 2393299Notes

Reaction equation

[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[N+:24]([C:27]1[C:36]2[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=2[CH:30]=[CH:29][C:28]=1[O:37][CH2:38][CH2:39][CH2:40]Br)([O-:26])=[O:25]>O>[N+:24]([C:27]1[C:36]2[CH2:35][CH2:34][CH2:33][CH2:32][C:31]=2[CH:30]=[CH:29][C:28]=1[O:37][CH2:38][CH2:39][CH2:40][N:10]1[CH2:11][CH2:12][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)([O-:26])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Phenylpiperazine (2.77 g, 17.1 mmol), potassium carbonate (7.1 g, 51.4 mmol) and N,N-dimethylformamide (30 ml) were added to 5,6,7,8-tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene (4.8 g, 15.3 mmol) and the mixture was stirred at 60° C. for 8 hours. The reaction mixture was added with water (80 ml) and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 200 g, eluent: hexane/ethyl acetate=7/1 to 3/1) to give 5,6,7,8-tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl) propoxy]naphthalene (5.5 g).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated
customThe residue was purified by silica gel chromatography (Wako Gell C-300: 200 g, eluent: hexane/ethyl acetate=7/1 to 3/1)

Sources & evidence

ORD record: ord-8c678bd06bef4a43ae18975ff76c8d60
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807860

Reaction notes

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