Hydrochloric Acid → 3-[1-(1-Methyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione hydrochloride

HRID 2258594Notes

Reaction equation

HRID 2258594 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=3[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[CH:9]2)[CH2:4][CH2:3]1.[ClH:34]>C(OCC)(=O)C.CO>[ClH:34].[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[C:18](=[O:33])[NH:19][C:20](=[O:32])[C:21]=3[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[CH:23]=3)=[CH:9]2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 98893513-[1-(1-Methyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione

Product 1

HCID 229072523-[1-(1-Methyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice cooled solution of 3-[1-(1-methyl-piperidin-4-yl)-1H-indol-3-yl]-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (70 g, 0.16 mol) in ethyl acetate (4 L) was saturated with gaseous hydrogen chloride for 3 hours. The precipitate formed was isolated by suction filtration, suspended in methanol (3 L) and stirred for 30 minutes. The mixture turned into a homogenous slurry, which was concentrated and treated with ether (500 mL). The title compound crystallized and was collected by suction filtration. The filter was vacuum dried over night (100° C./0.1 mm. Yield 70 g (92% of theory). M.Pt.: 280°-282° C.

Workup

  1. customThe precipitate formed
  2. customwas isolated by suction filtration
  3. concentrationwas concentrated
  4. additiontreated with ether (500 mL)
  5. customThe title compound crystallized
  6. filtrationwas collected by suction filtration
  7. customdried over night (100° C./0.1 mm

Sources & evidence

ORD record
ord-35c9481894c74bdebe2a83443333ab4d
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

Loading…