Hydrochloric Acid → HCID 22566204, compound

HRID 1634246Notes

Reaction equation

HRID 1634246 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C1[O:18][C:12]([CH2:14][CH2:15][CH2:16]Cl)([CH3:13])OC1.C(=O)([O-])[O-].[K+].[K+].CC[C:27]([C:29](Cl)=[O:30])=[O:28].Cl.C[O-].[Na+]>CN(C)C=O.C1COCC1.CO.C(N(CC)CC)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:16][CH2:15][CH:14]([C:12](=[O:18])[CH3:13])[C:27](=[O:28])[C:29]2=[O:30])=[CH:4][CH:3]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 78074-BromoanilineHCID 11430Potassium CarbonateHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 10942334Sodium MethoxideHCID 11007880Butanoyl chloride, 2-oxo-

Product 1

HCID 22566204HCID 22566204, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Part A: 1-[4-bromophenyl]-4-acetyl-2,3-dioxopiperidine was prepared in four steps in 10% overall yield by the following sequence of reactions. Commercially available 4-bromoaniline was treated with commercially available 5-chloro-2-pentanone ethylene ketal in dimethylformamide in the presence of potassium carbonate for three days. The crude alkylated aniline was treated with ethyloxalyl chloride in THF the presence of triethylamine. Hydrolysis of the ketal was accomplished by treating with aqueous HCl and the resulting material was subjected to Dieckmann cyclization conditions (NaOMe, methanol). The crude dioxopiperidine was purified by flash chromatography (elution with 4:1 hexanes/ethylacetate) to afford the title compound. 1H NMR (dmso d6): δ 7.56 (d, 2H, J =8 Hz), 7.26 (d, 2H, J =8 Hz), 3.60 (t, 2H), 3.28 (t, 2H), 2.30 (s, 3H). LRMS (ES+): 281.0 (M+H)+.

Workup

  1. customoverall yield by the following sequence of reactions
  2. customThe crude dioxopiperidine was purified by flash chromatography (elution with 4:1 hexanes/ethylacetate)

Sources & evidence

ORD record
ord-8af08bcdc464452e9c19f10a6a5fd9d2
Source dataset
uspto-grants-2003_01
Patent number
US06506771B2

Reaction notes

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