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

HRID 1684895Notes

Reaction equation

HRID 1684895 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-83770fc1ca134efe9e0322f347d57a1b
Source dataset
uspto-grants-2012_04
Patent number
US08148364B2

Reaction notes

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