Hydrochloric Acid → 1-[2-(Benzofurazan-5-yl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine hydrochloride

HRID 1195675Notes

Reaction equation

HRID 1195675 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.Br[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]2[C:26]([CH:30]=1)=[N:27][O:28][N:29]=2.C(=O)(O)[O-].[Na+].Cl>C(O)C.C(OCC)(=O)C.[I-].[Li+]>[ClH:1].[N:29]1[O:28][N:27]=[C:26]2[CH:30]=[C:22]([CH2:21][CH2:20][N:16]3[CH2:17][CH2:18][CH:13]([C:11]([C:8]4[CH:9]=[CH:10][C:3]5[C:4]([CH:7]=4)=[N:5][O:6][N:2]=5)=[O:12])[CH2:14][CH2:15]3)[CH:23]=[CH:24][C:25]=12

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 117758995-(2-Bromoethyl)benzofurazanHCID 679163514-(Benzofurazan-5-carbonyl)piperidine hydrochloride

Product 1

HCID 679163441-[2-(Benzofurazan-5-yl)ethyl]-4-(benzofurazan-5-carbonyl)piperidine hydrochlorideYield 40.3%

Reagents, catalysts & solvents 3

HCID 66321Lithium iodideCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(Benzofurazan-5-carbonyl)piperidine hydrochloride (80 mg, 0.3 mmol), 5-(2-bromoethyl)benzofurazan (170 mg, 0.75 mmol), sodium bicarbonate (101 mg, 1.2 mmol) and lithium iodide (1 mg) in ethanol were heated under reflux for 19 hours, cooled and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /CH3OH/NH3 (Aq.); 98:2:0.2 to give a yellow solid. This was dissolved in ethyl acetate (2 ml), and ethanolic HCl (Ca. 1M, 1 ml) was added. The resulting solid was collected and dried in vacuo to give the hydrochloride as a white solid (50 mg, 40%), mp 226°-228° C.

Workup

  1. temperatureunder reflux for 19 hours
  2. temperaturecooled
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with CH2Cl2 /CH3OH/NH3 (Aq.)
  6. custom98:2:0.2 to give a yellow solid
  7. customThe resulting solid was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2148e4ced9f7442b85c974b23b1e804c
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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