Pyridine → HCID 19696100, compound

HRID 863535Notes

Reaction equation

HRID 863535 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]1[CH2:26][CH:25]([C:27]([NH2:29])=O)[CH2:24][CH2:23][N:18]12.N1C=CC=CC=1>O1CCOCC1>[CH:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]1[CH2:26][CH:25]([C:27]#[N:29])[CH2:24][CH2:23][N:18]12

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 19696130HCID 19696130, compound

Product 1

HCID 19696100HCID 19696100, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

25.7 g (126 mmol) of trifluoroacetic anhydride were added dropwise to a stirred suspension of 26.5 g (123 mmol) of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxamide and 23.4 g (300 mmol) of pyridine in 500 ml of dry dioxane at 10° C. After completion of the addition, the solvent was removed under reduced pressure and the residue was crystallized from methanol to give 13 g of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8(RS)-carbonitrile, as a light tan solid of melting point 106°-109° C.

Workup

  1. additionAfter completion of the addition
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-e978b3177da643b1be8837763730cfcf
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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