Piperidine → N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide

HRID 24409

Reaction equation

HRID 24409 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:22]([NH:25][C:26]1[CH:34]=[C:33]2[C:29]([CH2:30][C:31](=[O:35])[NH:32]2)=[CH:28][CH:27]=1)(=[O:24])[CH3:23].N1CCCCC1.C(OCC)(=O)C>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[CH:8]=[C:30]1[C:29]2[C:33](=[CH:34][C:26]([NH:25][C:22](=[O:24])[CH3:23])=[CH:27][CH:28]=2)[NH:32][C:31]1=[O:35])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 2749839N-(2-Oxoindolin-6-yl)acetamideHCID 225710723-Tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde

Product 1

HCID 53907275N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamideYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-tert-butyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.25 g), 6-acetamido-2-oxindole (0.16 g) and piperidine (0.43 ml) in ethanol (3 ml) was held in a sealed tube at 100° C. for 12 hours. The reaction was cooled, added to ethyl acetate (250 ml), washed with 1N hydrochloric acid (100 ml) and brine (100 ml), dried with magnesium sulfate and concentrated. Some product went into the acid wash, so this was basified with solid sodium bicarbonate to pH 9 and extracted with ethyl acetate (2×150 ml). The organic layers were dried over magnesium sulfate, combined with the oil from the first crop of product and concentrated. Chromatography (silica, 40% ethyl acetate followed by 5-10% methanol/methylene chloride) afforded 100 mg (27%) of N-{3-[3-tert-butyl-4-(2-morpholin-4-ylethoxy) benzylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-acetamide as a yellow solid.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with 1N hydrochloric acid (100 ml) and brine (100 ml)
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. washwash
  6. extractionextracted with ethyl acetate (2×150 ml)
  7. dry with materialThe organic layers were dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1544f1db1a5e47a6b52225f05d1fcb4c
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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