Lithium iodide → 1-[2-(4-Nitrophenyl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine hydrochloride

HRID 1195676Notes

Reaction equation

HRID 1195676 reaction equation
[ClH:1].[N:2]1[O:6][N:5]=[C:4]2[CH:7]=[C:8]([C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[O:12])[CH:9]=[CH:10][C:3]=12.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([CH2:26][CH2:27]Br)=[CH:24][CH:23]=1)([O-:21])=[O:20].C(=O)(O)[O-].[Na+].[I-].[Li+]>C(O)C>[ClH:1].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([CH2:26][CH2:27][N:16]2[CH2:17][CH2:18][CH:13]([C:11]([C:8]3[CH:9]=[CH:10][C:3]4[C:4]([CH:7]=3)=[N:5][O:6][N:2]=4)=[O:12])[CH2:14][CH2:15]2)=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 66321Lithium iodideHCID 792664-Nitrophenethyl bromideHCID 516892Sodium BicarbonateHCID 679163514-(Benzofurazan-5-carbonyl)piperidine hydrochloride

Product 1

HCID 679164371-[2-(4-Nitrophenyl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the manner described in Example 14, 4-(benzofurazan-5-carbonyl)piperidine hydrochloride (80 mg, 0.3 mmol), 4-nitrophenethyl bromide (172 mg, 0.75 mmol), sodium bicarbonate (101 mg, 1.2 mmol), and lithium iodide (1 mg) in ethanol (3 ml) under reflux for 3 hours gave, after purification by flash column chromatography on silica gel, eluting with CH2Cl2 /CH3OH/NH3 (Aq.); 96:4:0.4 and treatment with ethanolic HCl, the hydrochloride as a white solid (44 mg, 35%), mp 238°-240° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customgave
  3. customafter purification by flash column chromatography on silica gel
  4. washeluting with CH2Cl2 /CH3OH/NH3 (Aq.)

Sources & evidence

ORD record
ord-4e2807ca03424b35a8fb56d0c54070f7
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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