Piperidine → HCID 69665633, compound

HRID 1829062Notes

Reaction equation

HRID 1829062 reaction equation
[N:1]([CH2:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])[O:6]1)=[C:2]=[O:3].[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[O:23]=[C:15]1[C:14](=[C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]([CH2:4][NH:1][C:2]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:3])[O:6]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86590934HCID 86590934, compound

Product 1

HCID 69665633HCID 69665633, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(3-isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (95 mg, 0.31 mmol) and piperidine (92.8 μl, 0.94 mmol) in THF (2.0 ml) was stirred at room temperature for 4 hours. The reaction was partitioned between EtOAc and water. The organic layer was washed with dilute HCl aqueous solution, water, saturated NaHCO3 aqueous solution, water, brine, dried with anhydrous Na2SO4, and rotary evaporated to a brown film. The brown film was chromatographed through silica gel column (CHCl3 to 4% MeOH/CHCl3 gradient) to produce piperidine-1-carboxylic acid [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-ylmethyl]-amide as a yellow solid (30 mg, 25%).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with dilute HCl aqueous solution, water, saturated NaHCO3 aqueous solution, water, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customrotary evaporated to a brown film
  5. customThe brown film was chromatographed through silica gel column (CHCl3 to 4% MeOH/CHCl3 gradient)

Sources & evidence

ORD record
ord-05260c46fa9846e08648d722f171fba9
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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