1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 2-{2-{3-[1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2-oxobenzimidazol-1-yl}ethyl}isoindole-1,3-dione

HRID 331235Notes

Reaction equation

HRID 331235 reaction equation
[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[H-].[Na+].Br[CH2:32][CH2:33][N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44].[Cl-].[NH4+]>CN(C=O)C>[CH:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[N:21]([CH2:32][CH2:33][N:34]4[C:35](=[O:44])[C:36]5[C:37](=[CH:40][CH:41]=[CH:42][CH:43]=5)[C:38]4=[O:39])[C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

6

Reactant 4

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 593229691-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 687036292-{2-{3-[1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2-oxobenzimidazol-1-yl}ethyl}isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[1-(1,2,2a,3,4,5-Hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol 2-one (1.00 g) was dissolved in DMF (30 ml), 60% sodium hydride (140 mg) was added, and the suspension was stirred for 1 hr. Then, N-(2-bromoethyl)phthalimide (818 mg) was added, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to room temperature, and poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 2-{2-{3-[1-(1,2,2a,3,4,5-hexahydroacenaphthylen-1-yl)piperidin-4-yl]-1,3-dihydro-2-oxobenzimidazol-1-yl}ethyl}isoindole-1,3-dione.

Workup

  1. stirringthe mixture was stirred at 100° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e67890f7f9be44d29253e60d358a54fe
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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