1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-[4-(5,6,7,8-Tetrahydro-quinoxalin-5-ylamino)-butyl]-isoindole-1,3-dione

HRID 899668Notes

Reaction equation

HRID 899668 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([NH2:11])[C:5]=2[N:4]=[CH:3][CH:2]=1.[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[CH2:23][CH2:24][CH2:25][CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([NH:11][CH2:26][CH2:25][CH2:24][CH2:23][N:14]3[C:15](=[O:22])[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:13]3=[O:12])[C:5]=2[N:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 120990635,6,7,8-Tetrahydroquinoxalin-5-amine

Product 1

HCID 691785752-[4-(5,6,7,8-Tetrahydro-quinoxalin-5-ylamino)-butyl]-isoindole-1,3-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,6,7,8-tetrahydroquinoxalin-5-ylamine (313 mg, 2.09 mmol) in CH2Cl2 (20 mL) at room temperature under inert atmosphere was added 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (227.8 mg, 1.05 mmol) followed by sodium triacetoxyborohydride (444 mg, 2.10 mmol). The reaction mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate solution (10 mL) was added and the mixture was extracted with dichloromethane (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated. The resultant material was purified by column chromatography on silica gel (10:1:0.5 CH2Cl2: MeOH: NH4OH) to provide the product as a clear oil (298 mg, 81%): 1H NMR (CDCl3): δ 1.56-1.66 (m, 2H), 1.70-1.95 (m, 4H), 2.04-2.22 (m, 4H), 2.71-2.85 (m, 2H), 2.87-3.05 (m, 2H), 7.69-7.73 (m, 2H), 7.80-7.85 (m, 2H), 8.34 (br s, 2H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resultant material was purified by column chromatography on silica gel (10:1:0.5 CH2Cl2: MeOH: NH4OH)

Sources & evidence

ORD record
ord-5cd853957a5d4a5eb752718553084aef
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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