Ammonium Chloride → (+/-) 2-(2-Amino-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione hydrochloride

HRID 217883Notes

Reaction equation

HRID 217883 reaction equation
CO[C:3]1[CH:8]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH2:7][CH2:6][CH2:5][N:4]=1.[Cl-:20].[NH4+:21]>CO>[ClH:20].[NH2:21][C:3]1[CH:8]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH2:7][CH2:6][CH2:5][N:4]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 67265802(+/-)2-(2-methoxy-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67265827(+/-) 2-(2-Amino-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 23.224 g (89.92 mMol) of (+/−)2-(2-methoxy-3,4,5,6-tetrahydropyridin-3-yl)-1H-isoindole-1,3(2H)-dione dissolved in 409 mL of methanol was added at room temperature 4.81 g (89.92 mmol) of ammonium chloride. The resulting mixture was stirred under reflux for 12 h. The cooled solution was evaporated to remove solvent. The residue was triturated with diethyl ether and filtered to afford 23.8 g (95%) of the pure product as a white powder.

Workup

  1. temperatureunder reflux for 12 h
  2. customThe cooled solution was evaporated
  3. customto remove solvent
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-08f51cc761494d8dbbbf24793b648b61
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

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