HCID 67087199, compound → HCID 67087296, compound

HRID 390384Notes

Reaction equation

HRID 390384 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]3([CH2:15][CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12][CH2:11]3)[CH2:9][N:8]([CH3:26])[C:7]=12>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][N:8]([CH3:26])[C:7]=12

Participants

3

Reactant 1

HCID 67087199HCID 67087199, compound

Product 1

HCID 67087296HCID 67087296, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of benzyl 7-chloro-1-methyl-spiro[indoline-3,4′-piperidine]-1′-carboxylate (1.1 g, 2.96 mmol) in trifluoroacetic acid (10 mL) is refluxed for 3 hours. The reaction mixture is concentrated, the pH of the residue is adjusted with 10% NaHCO3 (20 mL) to basic and extracted with EtOAc (3×20 mL). The combined extracts are washed with 10% NaHCO3 (20 mL), water (20 mL), and brine solution (20 mL), dried with a drying agent, filtered, and evaporated to dryness to give the title compound as a brown liquid (0.73 g, 103.9% crude). ESI/MS m/z 237.1 (M+H)+.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined extracts are washed with 10% NaHCO3 (20 mL), water (20 mL), and brine solution (20 mL)
  4. customdried with a drying agent
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7d91e5b7ca814c6898cf8c7c7a2392bc
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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