1-(2-Nitrophenyl)spiro[indoline-3,4'-piperidine]hydrochloride → HCID 12801640, compound

HRID 67223Notes

Reaction equation

HRID 67223 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:12]1)([O-])=O>Cl.CO.[Fe]>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]2([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[CH2:12]1

Participants

5

Reactant 1

HCID 128016381-(2-Nitrophenyl)spiro[indoline-3,4'-piperidine]hydrochloride

Product 1

HCID 12801640HCID 12801640, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

3.76 g of iron powder is added portionwise to a rapidly stirred ice cold slurry of 7.66 g of 1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]hydrochloride of Example 38 in 11.8 ml of concentrated hydrochloric acid and 300 ml of methanol. After heating at reflux for 3 hours, the reaction mixture (at room temperature) is filtered, made basic using 10% aqueous sodium hydroxide and extracted with chloroform. The organic phase is filtered through a pad of celite on a sintered glass funnel and the filtrate is washed with brine, dried over anhydrous sodium sulfate and concentrated to give 4.50 g of the crude free base of the product. Conversion to the hydrochloric acid salt with dichloromethane-ether/ethereal hydrochloric acid and two recrystallizations from hot isopropanol-methanol affords 1-(2-aminophenyl)spiro[indoline-3,4'-piperidine]dihydrochloride, mp 282.5° C., dec.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3 hours
  3. filtrationthe reaction mixture (at room temperature) is filtered
  4. extractionextracted with chloroform
  5. filtrationThe organic phase is filtered through a pad of celite on a sintered glass funnel
  6. washthe filtrate is washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto give 4.50 g of the crude free base of the product
  10. customConversion to the hydrochloric acid salt with dichloromethane-ether/ethereal hydrochloric acid and two recrystallizations from hot isopropanol-methanol

Sources & evidence

ORD record
ord-c30af6fcb21b46499290211b855628e3
Source dataset
uspto-grants-1982_08
Patent number
US04345081

Reaction notes

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