Piperidine → 3-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acid

HRID 24524Notes

Reaction equation

HRID 24524 reaction equation
[N:1]1([C:7]2[CH:15]=[C:14]3[C:10]([CH2:11][C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:17]([C:19]1[NH:20][C:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=2[C:27]=1[CH2:28][CH2:29][C:30]([OH:32])=[O:31])=O.N1CCCCC1>C(O)C>[N:1]1([C:7]2[CH:15]=[C:14]3[C:10]([C:11](=[CH:17][C:19]4[NH:20][C:21]5[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=5[C:27]=4[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:12](=[O:16])[NH:13]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 106090023-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acidHCID 219256916-(Morpholin-4-yl)-2-oxindole

Product 1

HCID 697649383-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acidYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4 g of 6-(morpholin-4-yl)-2-oxindole, 3.75 g of 3-(2-formyl-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid, and 1.8 mL of piperidine in ethanol (60 mL) was refluxed for 6 hrs. The reaction mixture was concentrated and acidified with 6 N hydrochloric acid to pH 6. The precipitate was collected by filtration, washed once with water, twice with ethyl acetate and twice with methanol to give 2.6 g of 3-[2-(6-Morpholin-4-yl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4,5,6,7-tetrahydro-1H-indol-3-yl]propionic acid as an orange solid (34% yield).

Workup

  1. temperaturewas refluxed for 6 hrs
  2. concentrationThe reaction mixture was concentrated
  3. filtrationThe precipitate was collected by filtration
  4. washwashed once with water, twice with ethyl acetate and twice with methanol

Sources & evidence

ORD record
ord-4ca6a836d4ed43619a19e2778862cbd7
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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