Trifluoroacetic acid → HCID 18630917, compound

HRID 1059700Notes

Reaction equation

HRID 1059700 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11023310HCID 11023310, compound

Product 1

HCID 18630917HCID 18630917, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-quinolin-2-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.072 g, 0.23 mmol) in methylene chloride (5 mL) was added dropwise to a solution of trifluoroacetic acid at 0° C. under N2. After stirring for 45 minutes. at 0° C., the reaction was concentrated to a yellow oil which was slurried in 5% sodium carbonate (5 mL) and stirred for 30 minutes. at ambient temperature. The mixture was concentrated to a yellow solid; the solid was triturated with chloroform (20 mL) which was dried over sodium sulfate. Concentration yielded 2-(1,2,3,6-tetrahydro-pyridin-4-yl)-quinoline (46 mg, 96%) as a yellow oil which was used without further purification. 1H NMR CDC13 δ 8.06 (d, J=9 Hz, 1H), 8.03 (d, J=9 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.68-7.63 (m, 1H), 7.55 (d, J=9 Hz, 1H), 7.46 (t, J=8 Hz, 1H), 6.75-6.40 (m, 1H), 3.70-3.65 (m, 2H), 3.42-3.29 (m, 1H), 3.20 (t, J=6 Hz, 2H), 2.85-2.78 (m, 2H).

Workup

  1. concentrationat 0° C., the reaction was concentrated to a yellow oil which
  2. stirringstirred for 30 minutes
  3. customat ambient temperature
  4. concentrationThe mixture was concentrated to a yellow solid
  5. customthe solid was triturated with chloroform (20 mL) which
  6. dry with materialwas dried over sodium sulfate
  7. concentrationConcentration

Sources & evidence

ORD record
ord-a87eb9d630474c329b25de3a71764daf
Source dataset
uspto-grants-2003_02
Patent number
US06521630B1

Reaction notes

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