Ethyl Oxo(Piperidin-1-Yl)Acetate → ethyl 2-(4-nitro-1H-indol-3-yl)-2-oxoacetate

HRID 551007Notes

Reaction equation

HRID 551007 reaction equation
P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([O-:12])=[O:11].N1([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])CCCCC1>>[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:16][NH:17]2)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 104406Ethyl Oxo(Piperidin-1-Yl)AcetateHCID 1457664-Nitro-1H-indoleHCID 4432411Diphosphoryl tetrachloride

Product 1

HCID 14131875ethyl 2-(4-nitro-1H-indol-3-yl)-2-oxoacetate

Procedure

Diphosphoryl chloride (23.5 mL, 170 mmol) was added dropwise to a stirred mixture of 4-nitroindole (25.0 g, 154 mmol) and ethyl 1-piperidineglyoxylate (29.0 g, 170 mmol) at 0° C. The mixture was allowed to warm slowly to ambient temperature and stirring was continued for 18 h. The reaction mixture was cooled to 0° C. and quenched carefully by addition of EtOH (50 mL), followed by saturated aqueous NaHCO3 until no further effervescence was observed. The precipitated yellow solid was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=263 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched carefully by addition of EtOH (50 mL)
  3. customThe precipitated yellow solid was isolated by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-92830f1cdf3b41fe93642a6f6b0eca62
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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