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

HRID 2393299
Notes
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Reaction equation

HRID 2393299 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 189755045,6,7,8-Tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene

Product 1

HCID 189755025,6,7,8-Tetrahydro-1-nitro-2-[3-(4-phenyl-1-piperazinyl)propoxy]naphthaleneYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes