Succinic anhydride → HCID 68776205, compound

HRID 1876811Notes

Reaction equation

HRID 1876811 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[NH:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:27]1(=[O:33])[O:32][C:30](=[O:31])[CH2:29][CH2:28]1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH:21]3[CH:16]([CH2:17][CH2:18][CH2:19][CH:20]3[N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:15]([C:27](=[O:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 687760732-(3,4-dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one

Product 1

HCID 68776205HCID 68776205, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (108.6 mg, 0.27 mmol) was dissolved in absolute CH2Cl2 (14 ml) under N2 in a 50 ml Schlenk flask. Succinic anhydride (33 mg, 0.33 mmol) and a spatula-tip of 4-(dimethylamino)pyridine (DMAP) were added to the solution. The mixture was stirred at room temperature overnight. The mixture was then evaporated almost to dryness in vacuo and the residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 8:2:0.1, l=17 cm, V=5 ml). The fractions with the product were evaporated in vacuo and the residue was taken up in CH2Cl2 again. The mixture was filtered with a glass filter crucible G4 and Celite and the filtrate was evaporated in vacuo. The yield gave a yellowish solid.

Workup

  1. customThe mixture was then evaporated almost to dryness in vacuo
  2. customthe residue was purified by flash chromatography (Ø 2 cm, CH2Cl2/MeOH/NH3 8:2:0.1, l=17 cm, V=5 ml)
  3. customThe fractions with the product were evaporated in vacuo
  4. filtrationThe mixture was filtered with a glass
  5. filtrationfilter crucible G4 and Celite
  6. customthe filtrate was evaporated in vacuo
  7. customThe yield gave a yellowish solid

Sources & evidence

ORD record
ord-5bad88fa6feb4ae58b830ae416928da4
Source dataset
uspto-grants-2012_11
Patent number
US08309725B2

Reaction notes

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