Hydrochloric Acid → 5,6-Diamino-2-(1-methylpiperidin-4-yl)isoindoline-1-one

HRID 929094Notes

Reaction equation

HRID 929094 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=O)[N:6]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[C:5]2=[O:22].[Sn].Cl>CCO>[NH2:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[NH2:1])[C:5](=[O:22])[N:6]([CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5352426Tin atom2×HCID 597617675-Amino-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione

Product 1

HCID 597617095,6-Diamino-2-(1-methylpiperidin-4-yl)isoindoline-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-amino-2-(1-methyl-piperidin-4-yl)-6-nitro-isoindole-1,3-dione (10.0 g, 32.9 mmol), tin powder (39.7 g, 329 mmol), EtOH (300 mL) and conc. HCl (100 mL) was stirred at 75° C. for 4 h. After cooling to RT excess of Tin was removed by filtration, the filtrate was evaporated. The residue was dissolved in CH2Cl2-MeOH (1:1) mixture, basified with NH4OH. Precipitate formed was removed by filtration, SiO2 was added to the filtrate, stirred for 1 h, the solvent was evaporated, the residue was loaded onto SiO2 (500 g) column. Eluted with CH2Cl2-MeOH—NH4OH (gradient from 100:0:0 to 100:10:1 v/v). Yield 7.86 g (30.2 mmol, 92%) as beige solid. LCMS [M+H]+ 261.4.

Workup

  1. customwas removed by filtration
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in CH2Cl2-MeOH (1:1) mixture
  4. customPrecipitate formed
  5. customwas removed by filtration, SiO2
  6. additionwas added to the filtrate
  7. stirringstirred for 1 h
  8. customthe solvent was evaporated
  9. washEluted with CH2Cl2-MeOH—NH4OH (gradient from 100:0:0 to 100:10:1 v/v)

Sources & evidence

ORD record
ord-cd51f68045ff4432b97ab7b4cb1d9074
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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