Indole-5-carbonitrile → HCID 18407073, compound

HRID 1016496Notes

Reaction equation

HRID 1016496 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1CCCC1>C(O)C>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH:21]=[C:22]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:8][CH:7]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 27513Indole-5-carbonitrileHCID 31268PyrrolidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 18407073HCID 18407073, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of 5-cyanoindole (10.0 g, 70.3 mmol), t-butyl-4-oxo-1-piperidinecarboxylate (15.4 g, 77.3 mmol), and pyrrolidine (14.7 mL, 175.7 mmol) in ethanol (200 mL) was heated at reflux for 20 hours then cooled to 0° C. The resulting precipitate was collected by vacuum filtration and rinsed with cold ethanol and hexanes to afford the product as a white solid (15.4 g, 68%).

Workup

  1. temperatureat reflux for 20 hours
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washrinsed with cold ethanol and hexanes

Sources & evidence

ORD record
ord-9b3b181c8f5346aaac2e654e04f62fdb
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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