Pyrrolidine → HCID 18407063, compound

HRID 1016502Notes

Reaction equation

HRID 1016502 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N1CCCC1>C(O)C>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 871116-ChloroindoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 18407063HCID 18407063, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-chloroindole (455 mg, 3.0 mmol), t-butyl-4-oxo-1-piperidinecarboxylate (650 mg, 3.3 mmol), and pyrrolidine (0.62 mL, 7.4 mmol) in ethanol (10 mL) was heated at reflux for 16 hours. Solvent was evaporated and the residue was recrystallized from ethyl acetate and hexanes to afford a yellow solid (721 mg, 72%).

Workup

  1. temperatureat reflux for 16 hours
  2. customSolvent was evaporated
  3. customthe residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-f53188511b2344849a70d10c887ac787
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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