Benzenamine hydrochloride (1:1) → HCID 14767301, compound

HRID 1088932Notes

Reaction equation

HRID 1088932 reaction equation
[CH2:1]([CH:5]1[CH2:9][C:8]2([CH2:13][CH:12]([CH2:14][CH2:15][CH2:16][CH3:17])C(=O)[C:10]2=[O:19])[C:7](=[O:20])C1=O)[CH2:2][CH2:3][CH3:4].Cl.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>NC1C=CC=CC=1>[CH2:14]([CH:12]1[CH2:13][C:8]2([CH2:9][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]2=[O:20])[C:10](=[O:19])[N:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 8870Benzenamine hydrochloride (1:1)HCID 22162374HCID 22162374, compound

Product 1

HCID 14767301HCID 14767301, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6115AnilineSolvent

Procedure

A mixture of 53.6 g (0.02 mole) of 3,8-dibutyl-2,7-dioxospiro-[4.4]nonane-1,6-dione, 10.32 g (0.08 mole) of aniline hydrochloride and 40 ml of aniline was placed in a 500 ml round bottom flask and heated to reflux. After refluxing for 6 hours, the aniline was removed by distillation at reduced pressure. The resulting mixture was subjected to column chromatography employing a 2:1 mixture of diethyl ether and petroleum ether as eluent. The product, 3,8-dibutyl-2,7-diphenyl-2,7-diazaspiro[4.4]nonane-1,6-dione, was isolated as a viscous oil in a yield of about 86%. The infrared, 13C-NMR and mass spectra of the product were consistent with this structure.

Workup

  1. customwas placed in a 500 ml round bottom flask
  2. temperatureheated to reflux
  3. temperatureAfter refluxing for 6 hours
  4. customthe aniline was removed by distillation at reduced pressure
  5. additiona 2:1 mixture of diethyl ether and petroleum ether as eluent

Sources & evidence

ORD record
ord-33ef4e5b385b474d8b0792c78511765e
Source dataset
uspto-grants-1990_10
Patent number
US04963691

Reaction notes

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