Hydrochloric Acid → 1-(2-Nitrophenyl)spiro[indoline-3,4'-piperidine]hydrochloride

HRID 67222Notes

Reaction equation

HRID 67222 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N+:23]([O-:25])=[O:24])[CH2:9]2)[CH2:5][CH2:4]1)#N.[OH-].[Na+].[ClH:28]>C(O)(=O)C>[ClH:28].[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]2([CH2:5][CH2:4][NH:3][CH2:8][CH2:7]2)[CH2:9]1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 128016151'-Cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A slurry of 14.62 g of 1'-cyano-1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine] of Example 37 in 100 ml of glacial acetic acid and 190 ml of 3 N aqueous hydrochloric acid is heated at reflux for 18 hours, the mixture becomes homogeneous at 70°-80° C. The mixture is made basic using aqueous sodium hydroxide and extracted with chloroform. The organic portions are combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated to give a solid comprising the free base of the product. The salt is prepared from the freshly alkali washed and dried free base using chloroform/ethereal hydrochloric acid, to yield the product mp. 222°-224° C. of 1-(2-nitrophenyl)spiro[indoline-3,4'-piperidine]hydrochloride.

Workup

  1. temperatureat reflux for 18 hours
  2. custombecomes homogeneous at 70°-80° C
  3. extractionextracted with chloroform
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a solid comprising the free base of the product
  8. customThe salt is prepared from the
  9. washfreshly alkali washed
  10. customdried free base

Sources & evidence

ORD record
ord-d14ee491169940fd9e4ea3f6d40ed955
Source dataset
uspto-grants-1982_08
Patent number
US04345081

Reaction notes

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